117252-96-7Relevant academic research and scientific papers
Sulfuric acid immobilized on silica: an efficient promoter for one-pot acetalation-acetylation of sugar derivatives
Mukhopadhyay, Balaram
, p. 4337 - 4341 (2007/10/03)
Sulfuric acid immobilized on silica gel has been used as an efficient and safe alternative promoter for acetalation and subsequent acetylation of sugar glycosides using stoichiometric reagents without work-up. The synthesis of different types of per-O-ace
Linkable sialyl lewis x analogs
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, (2008/06/13)
Disclosed herein is a class of linkable tetrasaccharide compounds that includes the amino phenyl glycoside of sialyl Lewis X (SLeX) and related analogs. These compounds have conjugatable nucleophilic groups, making them useful in preparing mult
Biosynthetic studies on the α-glucosidase inhibitor acarbose: The chemical synthesis of dTDP-4-amino-4,6-dideoxy-α-D-glucose
Bowers, Simeon G.,Mahmud, Taifo,Floss, Heinz G.
, p. 297 - 304 (2007/10/03)
To study the biosynthesis of the pseudotetrasaccharide acarbose, dTDP-4-amino-4,6-dideoxy-α-D-glucose (3) was prepared from galactose in 16 steps. After initial protecting-group manipulations, the 6-position of galactose was deoxygenated by hydride displa
Synthesis of 2-(trimethylsilyl)ethyl 4-C-methyl-β-D-glucopyranuronamide. A derivative suitable as building block in synthesis of phosphoglycolipid antibiotics
Hansson,Plobeck
, p. 11319 - 11326 (2007/10/02)
The title compound, a protected derivative of a unique component in the moenuronamide group of phosphoglycolipid antibiotics has been synthesised in eleven steps and 30% total yield from 2-(trimethylsilyl)ethyl-β-D-galactopyranoside (6). The key step was
2-(Trimethylsilyl)ethyl Glycosides. Synthesis, Anomeric Deblocking, and Transformation into 1,2-Trans 1-O-Acyl Sugars
Jansson, Karl,Ahlfors, Stefan,Frejd, Torbjoern,Kihlberg, Jan,Magnusson, Goeran,et al.
, p. 5629 - 5647 (2007/10/02)
Twenty-seven mono --> tetrasaccharidic 2-(trimethylsilyl)ethyl (TMSET) glycosides were synthesized by the Koenigs-Knorr-type method in combination with a wide range of standard reagents for glycoside synthesis and protecting-group chemistry.Variously protected TMSET glycosides were treated with BF3*Et2O (0.7-0.8 equiv) and different carboxylic anhydrides (1.1-15 equiv) in toluene at 22-55 deg C, which gave in one step the corresponding protected 1-O-acyl sugars.In the majority of cases, the yields of purified compounds exceeded 90percent and the anomeric configuration of the starting TMSET glyoside was conserved to a large extent (>95percent) in most of the 1-O-acylated products.Unprotected and acetyl-, benzoyl-, benzyl-, dimethyl-tert-butylsilyl-, and phthaloyl-protected mono-->tetrasaccharidic TMSET glycosides were anomerically deblocked by using trifluoroacetic acid in dichloromethane at 0-22 deg C for 10-30 min.The hemiacetal products were isolated in 88-96percent yield; all reagents and byproducts were volatile and easily removed.
