87119-49-1

Basic information

• Product Name: propyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside
• Synonyms: propyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside
• CAS NO: 87119-49-1
• Molecular Weight: 598.803
• Mol File: 87119-49-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: propyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: propyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside(87119-49-1)
• EPA Substance Registry System: propyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside(87119-49-1)

Safety Data

• Hazardous Substances Data: 87119-49-1(Hazardous Substances Data)

Upstream product

• 998-38-9 trithioboronic acid tripropyl ester 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 107-03-9 1-thiopropane 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Relevant articles and documents

Reversal of anomeric selectivity with O-glycosyl trichloroacetimidates as glycosyl donors and thiols as acceptors under acid/base catalysis

Boron trifluoride or trimethylsilyl trifluoromethanesulfonate catalysed the generation of thioglycosides from O-glucopyranosyl or O-galactopyranosyl trichloroacetimidates and thiols giving mainly or exclusively α-thioglycosides. However, the same reaction

Glycosylimidates, 8. - Synthesis of 1-Thioglycosides

As expected, the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration.The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides.The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.