114217-35-5

Basic information

• Product Name: methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside
• Synonyms: methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside
• CAS NO: 114217-35-5
• Molecular Weight: 432.589
• Mol File: 114217-35-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside(114217-35-5)
• EPA Substance Registry System: methyl 6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside(114217-35-5)

Safety Data

• Hazardous Substances Data: 114217-35-5(Hazardous Substances Data)

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 3396-99-4 methyl α-D-galactopyranoside 

Downstream Products

• 169686-78-6 Methyl 2,3-di-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside 
• 169686-81-1 Methyl 2,3,4-tri-O-acetyl-6-O-(tert-butyldiphenylsilyl)-α-D-galactopyranoside 
• 401593-03-1 methyl 2-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-galactopyranoside 
• 1598426-42-6 methyl 6-O-tert-butyldiphenylsilyl-2,4-di-O-benzoyl-α-D-galactopyranoside 
• 1222709-76-3 2,3,4-benzyloxy-6-((tert-butyldiphenylsilyl)oxy)methyl-α-D-galactose 
• 175844-96-9 2,3,4-Tri-O-benzyl-5,6-dideoxy-L-arabino-hex-5-enose 
• 1440526-70-4 (4S,5S,6S,7S)-5,6,7-tris(benzyloxy)cyclohept-2-enol 
• 1440526-69-1 (4R,5S,6S,7S)-5,6,7-tris(benzyloxy)cyclohept-2-enol 

Relevant articles and documents

INKT CELL MODULATORS AND METHODS OF USING THE SAME

Disclosed herein are α-galactosylceramide (α-GalCer) analogs and compositions thereof, methods of activating invariant Natural Killer T (iNKT) cells using said analogs, methods of treating diseases by activating iNKT cells using said analogs, and combinat

Imidazole-promoted 1,4-migration of the tert-butyldiphenylsilyl group: Influence on the selectivity control of the silylation reactions of carbohydrate OH groups

The regioselective protection of secondary hydroxy groups of gluco-, galacto-, manno-, rhamno- and fucopyranosides using TBDPSCl with imidazole in DMF has been studied. It was found that the relative spatial arrangement of the OH groups modulates the silylation selectivity which arises from the combination of kinetic factors and the intramolecular migrations of the secondary TBDPS groups. The rearrangement of the TBDPS groups has a much larger effect on the α-D-manno- and α-L-rhamnopyranosides, allowing the protection of the OH groups at positions 2, 3 or 2 and 4, in synthetically useful yields, by changing the reaction conditions. The relative reactivity of the secondary OH groups seems particularly likely to be governed by steric factors. This trend provides a valuable approach to the synthesis of 3-O-tert-butyldiphenylsilyl-1-thio-β-L-fucopyranoside.

Stereocontrolled lincomycin synthesis

The synthesis from methyl α-D-galactopyranoside (6) of methyl thiolincosaminide (2), the direct synthetic precursor to lincomycin (1), is presented. The key step for controlling the off-pyranose stereocenters C-6 and C-7 is a novel intramolecular nitrogen delivery reaction using epoxy alcohol 10. Reaction of 10 with dimethylcyanamide in the presence of sodium hydride and imidazole leads to the oxazoline 14, a protected vicinal amino alcohol. The synthesis is completed by efficient exchange of acetal for thioacetal, followed by hydrolysis of the oxazoline and removal of the benzyl groups. The target 2 is obtained in 22 steps and 28% overall yield from 6.