Chemoselective per-O-trimethylsilylation and homogeneous N-functionalisation of amino sugars

A highly efficient CH3CN-promoted hexamethyldisilazane per-O-trimethylsilylation of amino sugars was developed. Its applications in homogenous N-functionalisation and a concise synthesis of glucosamine 6-phosphate are described.

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Bibliographic Details
Published inChemical communications (Cambridge, England) Vol. 51; no. 1; pp. 104 - 106
Main Authors Joseph, A. Abragam, Dhurandhare, Vijay M., Chang, Chun-Wei, Verma, Ved Prakash, Mishra, Girija Prasad, Ku, Chiao-Chu, Lin, Chun-Cheng, Wang, Cheng-Chung
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 04.01.2015
Subjects
Acetonitriles - chemistry
Amino Sugars - chemistry
Chemistry
Chemistry, Multidisciplinary
Glucosamine - analogs & derivatives
Glucosamine - chemical synthesis
Glucosamine - chemistry
Glucose-6-Phosphate - analogs & derivatives
Glucose-6-Phosphate - chemical synthesis
Glucose-6-Phosphate - chemistry
Nitrogen - chemistry
Organosilicon Compounds - chemistry
Oxygen - chemistry
Physical Sciences
Pyridines - chemistry
Science & Technology
Sugars
Synthesis
ACID
THIOGLYCOSIDE
D-GLUCOSAMINE
GAS-LIQUID CHROMATOGRAPHY
BIS(OXAZOLINE) LIGAND
COFACTOR
GLYCOSYLATION
AZIDE
DERIVATIVES
ONE-POT PROTECTION
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Summary:A highly efficient CH3CN-promoted hexamethyldisilazane per-O-trimethylsilylation of amino sugars was developed. Its applications in homogenous N-functionalisation and a concise synthesis of glucosamine 6-phosphate are described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc06645f