371123-22-7

Basic information

• Product Name: phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside
• Synonyms: phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside
• CAS NO: 371123-22-7
• Molecular Weight: 271.337
• Mol File: 371123-22-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside(371123-22-7)
• EPA Substance Registry System: phenyl 2-amino-2-deoxy-1-thio-β-D-glucopyranoside(371123-22-7)

Safety Data

• Hazardous Substances Data: 371123-22-7(Hazardous Substances Data)

Upstream product

• 79528-49-7 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 56644-75-8 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranose 
• 169557-87-3 phenyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-trichloroacetamido-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 108-98-5 thiophenol 
• 371123-32-9 ((2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester 
• 128960-84-9 N-((3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2Hpyran-3-yl)acetamide 
• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 

Downstream Products

• 128960-84-9 N-((3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(phenylthio)tetrahydro-2Hpyran-3-yl)acetamide 
• 915154-77-7 C₄₆H₅₁N₃O₁₄ 
• 1394857-47-6 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 
• 277756-84-0 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 277756-86-2 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 277756-87-3 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 666753-83-9 phenyl 2-azido-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 1394857-33-0 phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 1394857-34-1 phenyl 2-azido-2-deoxy-3,6-di-O-benzyl-4-O-trichloroacetyl-1-thio-β-D-glucopyranoside 
• 1394857-35-2 phenyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-1-thio-4-trichloroacetyl-β-D-glucopyranoside 
• 1394857-41-0 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α/β-D-glucopyranoside 
• 1394857-42-1 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-β-D-glucopyranoside 
• 1394857-60-3 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-trichloroacetyl-1-O-trichloroacetimidate-α-D-glucopyranoside 

Relevant articles and documents

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

The practical synthesis of carbohydrate-based NHC-Rh complexes bearing C1 or C3 sterically differentiated positions, accessed by glycosylation or SNAr strategies, is reported. These catalysts exhibit pseudo-enantiomeric behaviour in the hydrosilylation of acetophenone. We show that steric bulk at C1 gives preference for (S)-phenyl-1-ethanol, while bulk at C3 leads to the (R)-enantiomer. These results represent the first example of pseudo-enantiomeric carbohydrate-based NHC ligands leading to enantiotopic discrimination.

Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable

Synthesis of a library of stereo- and regiochemically diverse aminoglycoside derivatives

A library of forty modified aminoglycosides was prepared in which the configuration and regiochemistry of two or three rings was widely varied. The library was based around three core ring systems: the 2-deoxystreptamine ring system found in the natural products, and both enantiomers of (1R*,2R*,4R*,5R*)-2,5-diamino-cyclohexane-1,4-diol and (1R*,3R*,4R*,6R*)-4,6-diaminocyclohexane-1,3-diol. In each case, the core was modified by glycosylation with one or two sugar rings. The absolute configuration of the sugar substituents (D or L), the configuration of the anomeric centres (α or β), and the regiochemical arrangement of the amine(s) were varied. The Royal Society of Chemistry 2005.