1st Edition
Carbohydrate Chemistry Proven Synthetic Methods, Volume 4
Volumes in the Proven Synthetic Methods Series address the concerns many chemists have regarding irreproducibility of synthetic protocols, lack of identification and characterization data for new compounds, and inflated yields reported in chemical communications—trends that have recently become a serious problem.
Featuring contributions from world-renowned experts and overseen by a highly respected series editor, Carbohydrate Chemistry: Proven Synthetic Methods, Volume 4 compiles reliable synthetic methods and protocols for the preparation of intermediates for carbohydrate synthesis or other uses in the glycosciences.
Exploring carbohydrate chemistry from both the academic and industrial points of view, this unique resource brings together useful information into one convenient reference. The series is unique among other synthetic literature in the carbohydrate field in that, to ensure reproducibility, an independent checker has verified the experimental parts involved by repeating the protocols or using the methods.
The book includes new or more detailed versions of previously published protocols as well as those published in not readily available journals. The essential characteristics of the protocols presented are reliability, updated characterization data for newly synthesized substances and the expectation of wide utility in the carbohydrate field. The protocols presented will be of wide use to a broad range of readers in the carbohydrate field and the life sciences, including undergraduates taking carbohydrate workshops.
Introduction
Vogel, C., Murphy, P
The Aim and Scope of this Series, and Information for Prospective Authors
Kováč, P.
Part I: Synthetic Methods
Chapter 1: Picoloyl protecting group in oligosaccharide synthesis: installation, H-bond-mediated aglycone delivery (HAD), and selective removal
Mannino, M. P., Yasomanee, J. P., Patteti, Demchenko. A. V.
Chapter 2: MMTr as an efficient S-protecting group in the manipulation of glycosyl thiols
Smith, R., Calatrava-Perez, E., Zhu, X.
Chapter 3: One-step Inversion of Configuration of a Hydroxyl Group in Carbohydrates
Manabe, S., Blaukopf, M.
Chapter 4: Formation and Cleavage of Benzylidene Acetals Catalyzed by NaHSO4∙SiO2
Sun, L., Wang, X., Ye, X.-S.,
Chapter 5: Thiodisaccharides by photoinduced hydrothiolation of 2-acetoxy glycals
Eszenyi, D., Lázár,L., McCourt, R. O., Borbás, A.
Chapter 6: One Step Preparation of Protected N-tert-Butanesulfinyl d-ribo and d-xylo furanosylamines from Related Sugar Hemiacetals
Cocaud, C., Nicolas, C., Désiré, J., Martin. O. R.
Chapter 7: An Alternative Preparation of Azides from Amines via Diazotransfer with Triflyl Azide
Ye, Y., Wang, X., Ye, X.-S.
Chapter 8: Simple Preparation of Dimethyldioxirane and its Use as Epoxidation Agent for the Transformation of Glycals to Glycosyl Phosphates
Kettelhoit, K., Sasmal, A., Liu, X., Gritsch, P., Werz, D. B.
Chapter 9: Preparation of O-perbenzoylated 2-bromo-2-deoxy-α-D-gluco-hept-2-ulopyranosonic acid derivatives
Nagy, V., Czifrák, K., Apelt, O., Juhász, L. Somsák, L.
Chapter 10: Preparation of 2,6-anhydro-hept-2-enonic acid derivatives and their 3-deoxy counterparts
Kun, S., Deák, S., Czifrák, K., Apelt, O., JuhEasz, L., Somsák, L.
Part II: Synthetic Intermediates
Chapter 11: Synthesis of 4-Nitrophenyl -d-Galactofuranoside. A Useful Substrate for -d-Galactofuranosidases
Marino, C., Poklepovich Caride, S., Villaume, S., de Lederkremer, R. M.
Chapter 12: Synthesis of benzoylated -D-glucosamine derivatives
Di Salvo, C., Fox, K., Langhanki, J., Murphy, P. V.
Chapter 13: Synthesis of 3,4,6-Tri-O-benzyl-2-deoxy-2-p-(toluenesulfonamido)--D-glucopyranose
Harit, V. K., Ramesh, N. G., Sampathkumar, S.-G.
Chapter 14: A Convenient Synthesis of 3,4-Di-O-Acetyl-D-Rhamnal (3,4-Di-O-Acetyl-6-Deoxy-D-Glucal)
Spradlin, J. N., Lloyd, D., Liang, C., Bennet, C. S.
Chapter 15: One-Pot Synthesis of 2-Acetamido-1,3,4,6-Tetra-O-Acetyl-2-Deoxy-β-D-Glucopyranose Using Anomeric O-Acylation
Pertel, S. S., Kakayan, E. S., Servi, S. A., McDonagh, A. W.
Chapter 16: Per-O-t-Butyldimethylsilyl-β-D-Galactofuranose: A Versatile Glycosylating Agent for Galactofuranosylation
Gonzales-Salas, D., Guberman, M., Marino, C.
Chapter 17: Per-O-benzoyl-1,2-O-benzylidene derivatives of pyranoses and furanoses – versatile building blocks for oligosaccharide synthesis
Abronina, P. A., Zinin, A. I., Podvalnyy, M .N., Pasari, S., Kononov, L. O.
Chapter 18: Synthesis of 1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-a ,-d-glucopyranose using the diazo-transfer reagent imidazole-1-sulfonyl azide hydrogen sulfate
Potter, G., T., Guazelli, L., Jayson, G. C., Miller, G. J., Gardiner, J. M.
Chapter 19: Synthesis of methyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α- and β-D-glucopyranosides
Henderson, A. S., Piferi, C., Galan, M. C.
Chapter 20: Ring-opening of benzylated gluconolactone to access useful gluconamide conjugates
Roy, S., Denavit, V., Shiao, T. C., Giguère, D.
Chapter 21: A Multigram Synthesis of Phenyl 2-Azido-3-O-Benzyl-2-Deoxy-4,6-O-Benzylidene-1-Thio-α-D-Mannopyranoside
Gagarinov, I. A., Wang, Z., Srivastava, A. D., Boons, G.-J.
Chapter 22: Preparation and characterization of 6-Azidohexyl 2,3,4,6-tetra-O-acetyl--D-glucopyranoside
Kushwaha, D., Baráth, M., Kováč, P.
Chapter 23: Synthesis of (2S,3S,4S)-2,3,4-tri-O-benzyl-5-bromopentanenitrile
Malik, M., Zawisza, A., Jarosz, S.
Chapter 24: Simplifying Access to 3,4-Di-O-Acetyl-D-Fucal
Gagarinov, I. A., Visansirikul, S., Srivastava, A. D., Boons, G.-J.
Chapter 25: 2-Chloroethyl and 2-Azidoethyl 2,3,4,6-Tetra-O-acetyl- -d-gluco- and -d-galactopyranosides
Reddy, A., Ramos-Ondono, J., Abbey, L., Velasco-Torrijos, T.
Chapter 26: Synthesis of heptakis(6-O-tert-butyldimethylsilyl) Cyclomaltoheptaose
Casas-Solvas, J. M., Malanga, M., Vargas-Berenguel, A.
Chapter 27: Sodium D-Galactonate, D-Galactono-1,4-Lactone and Synthetically Useful Methyl D-Galactonates
Rivas, V., Kolender, A. A., Duhirwe, G., Varela, O.
Chapter 28: Synthesis of a 3,6-orthogonally-protected mannopyranoside building block
Roy, S., Denavit, V., Lainé, D., Meyer, J., Giguère, D.
Chapter 29: Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(bis-methoxycarbonyl)-methyl]- -d-glucopyranoside
Pavashe, P., Pimpampalle, T., Juhász, L., Linker, T.
Chapter 30: Fluorine-containing carbohydrates: synthesis of 6-deoxy-6-fluoro-1,2:3,4-di-O-isopropylidene--D-galactopyranose
Denavit, V., Lainé, D., Le Heiget, G., Giguére, D.
Chapter 31: A facile synthesis of 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoroacetamido- -D-glucopyranose
Podvalnyy, N. M., Voznyi, Y. V., Zinin, A. I., Pistorio, S. G., Polina I. Abronina,P. I., KononovL. O.
Chapter 32: An expeditious route to an HO-4 free d-GalNAc building block from d-GlcNAc
Santoyo-Gonzalez, F., Hernandez-Mateo, F., Lopez-Jaramillo, F. J., Uriel, C.
Chapter 33: Improved Synthesis of 3-(2-Deoxy--d-erythro-pentofuranos-1-yl)prop-1-ene
Wächtler, H, Fuentes, P. D., Apelt, O., Michalik, D., Potopnyk, M. A., Vogel, C.
Chapter 34: Improved Synthesis of 3-(-d-Ribofuranos-1-yl)prop-1-ene
Wächtler, H., Fuentes, D. P., Apelt, O., Michalik, D.. Potopnyk, M. A., Vogel, C.
Chapter 35: 3-Azidopropyl 2-acetamido-2-deoxy-a -d-glucopyranoside
Farcet, J.-B., Herczeg, M., Christler, A., Kosma, P.
Chapter 36: Large Scale Synthesis of 2,3,4,6-Tetra-O-Benzyl-1-Deoxynojirimycin
Hazelard, D., Lepage, M. L., Schneider, J. P., Pichon, M. M., Massicot, F., Compain, P.
Chapter 37: Synthesis of Indol-3-yl Glucuronides for Monitoring Glucuronidase Activity
Böttcher, S., Czaschke, C., Pascolutti, M., Thiem, J.
Chapter 38: Preparation of 2,6-anhydro-3,4,5,7-tetra-O-benzyl-d-glycero-d-gulo-heptonimidamide
Szennyes, E., Bokor, E., Pascal, Y., Kiss, A., Somsák, L.
Chapter 39: Allyl 4,6-O-benzylidene-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside
Le Guen, Y. L., Le Heiget, G., Urban, D., CHassagne, P., Mulard, L. A.,
Chapter 40: 1,2-Bis(diphenylphosphano)ethane (DPPE)-Mediated Synthesis of Glycosyl Amides
Temelkoff, D. P., Gabba, A., Norris, P.
Biography
Christian Vogel earned a PhD in organic chemistry–heterocyclic chemistry under the supervision of Professor Klaus Peseke at the University of Rostock in 1980. Since 1992, he has served as a professor in the Department of Organic Chemistry, University of Rostock.
In addition to fucose chemistry, Dr. Vogel’s main interests are pectin fragment synthesis using the modular design principle, the synthesis of rare sugars for structural investigations, and C-nucleosides.
Paul V. Murphy was appointed to the position of Established Professor of Chemistry at National University of Ireland Galway (NUI Galway) in 2008. He is from the West of Ireland (Turloughmore, Co. Galway).
His group is engaged in the design and synthesis of bioactive compounds, with a focus on carbohydrates, maintaining a long tradition in carbohydrate research in Galway’s School of Chemistry.
'The contributors are the best scientists in the field and the series editor is highly respected. The volumes will ... be of use to undergraduates involved in carbohydrate workshops.'
– Alexei Demchenko, Associate Professor of Chemistry and Biochemistry, Director of Graduate Studies, University of Missouri – St. Louis.‘This essential book series, focused on carbohydrate synthesis, starts with a dedication to Nobel Laureate Sir John W. Cornforth, who is credited with the first public criticism of what he pictured as ‘pouring a large volume of unpurified sewage into the chemical literature.’1 Unfortunately, this issue is not limited to the field of chemistry as many high profile cases of irreproducible experiments have led to alarms being set off even in the popular press.2 This series then serves as the much-needed water treatment plants – places where the reader can be guaranteed a good clean reproducible experiment. … at least now chemists with or without expertise in carbohydrates can count on finding reliable procedures to make sugar-based compounds at one scale – a major achievement. Not only should current practitioners gain back time lost in attempts to properly reconstruct experimental procedures, but these procedures should also allow more creative scientists to contribute to this growing area.
- Cornforth JW. Austr. J. Chem. 1993;46:157e70.
- For example, see Unreliable research: trouble at the lab. Econ. October 19, 2013.’
– Nicola L.B. Pohl, Indiana University, Department of Chemistry, Bloomington, IN, USA, for Carbohydrate Research, http://dx.doi.org/10.1016/j.carres.2015.04.007.
