111902-03-5

Basic information

• Product Name: 3 6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-
• Synonyms: 3 6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-
• CAS NO: 111902-03-5
• Molecular Formula: C₁₈H₃₈O₄Si₂
• Molecular Weight: 374.66292
• Mol File: 111902-03-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 235 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.96g/cm³
• Refractive Index: n20/D 1.458(lit.)
• CAS DataBase Reference: 3 6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-(CAS DataBase Reference)
• NIST Chemistry Reference: 3 6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-(111902-03-5)
• EPA Substance Registry System: 3 6-DI-O-(TERT-BUTYLDIMETHYLSILYL)-D-(111902-03-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 111902-03-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H38O4Si2/c1-17(2,3)23(7,8)21-13-15-16(19)14(11-12-20-15)22-24(9,10)18(4,5)6/h11-12,14-16,19H,13H2,1-10H3/t14-,15-,16-/m1/s1

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 21193-75-9 D-galactal 

Downstream Products

• 1345819-40-0 3,6-di-O-tert-butyldimethylsilyl-1-O-(3-chlorobenzoyl)-α-D-galactopyranoside 
• 130257-56-6 methyl 4-O-(4-O-acetyl-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside 
• 130257-60-2 methyl 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-sulfo-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid, disodium salt 
• 130257-53-3 methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate 
• 130257-54-4 methyl -2,3-di-O-benzyl-β-D-glucopyranosid>uronate 
• 130257-55-5 (2S,3S,4S,5R)-6-Acetoxy-3-((2S,3R,4R,5R,6R)-5-acetoxy-3-acetylamino-4-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4,5-bis-benzyloxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 130278-31-8 methyl uronate 
• 130257-58-8 methyl 4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranoside 
• 130257-59-9 methyl 4-O-(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-galactopyranosyl)-2,3-di-O-benzyl-β-D-glucopyranosiduronic acid 

Relevant articles and documents

Syntheses of the methyl glycosides of the repeating units of chondroitin 4- and 6-sulfate.

3,4,6-Tri-O-acetyl-D-galactal was transformed into methyl 6-O-acetyl-2-azido-4-O-benzyl-2-deoxy-beta-D-galactopyranoside and its 4-O-acetyl-6-O-benzyl analogue, each of which was glycosylated with activated, O-acetylated derivatives of methyl D-glucopyranosyluronate. The resulting beta-(1----3)-linked disaccharide derivatives were each reductively N-acetylated, hydrogenolysed, O-sulfated, and saponified to afford the disodium salts of methyl 2-acetamido-2-deoxy-3-O-(beta-D-glucopyranosyluronic acid)-4-O-sulfo-beta-D-galactopyranoside and the 6-O-sulfo analogue. D-Galactal was also transformed into activated derivatives of 2-azido-3,6-di-O-benzyl-2-deoxy-D-galactopyranose and their 3,4-di-O-benzyl analogues with various substituents at O-4 and O-6. These glycosyl donors were condensed with 6-O-protected derivatives of methyl 2,3-di-O-benzyl-beta-D-glucopyranoside to give the beta-(1----4)-linked disaccharide derivatives, which were selectively deprotected, then oxidised at C-6 of the gluco unit, reductively N-acetylated, selectively deprotected, O-sulfated at C-4 or C-6 of the galacto unit, and hydrogenolysed to give the disodium salts of methyl 4-O-(2-acetamido-2-deoxy-4-O-sulfo-beta-D-galactopyranosyl)-beta-D- glucopyranosiduronic acid and the 6-O-sulfo analogue.