tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 153094-00-9
• Molecular Formula: C₁₉H₃₁N₃O₅Si
• Molecular Weight: 409.558
• Mol file: 153094-00-9.mol

Synonyms:tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 4 articles about tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside (138923-10-1) → tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-00-9)

Guidance literature:

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether;

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / p-TsOH / acetonitrile / 1 h

2: 76 percent / NaCNBH₃, mol. sieve 4A, HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; acetonitrile;

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → tert-Butyldimethylsilyl 2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside (153094-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / p-TsOH / acetonitrile / 1 h

2: 76 percent / NaCNBH₃, mol. sieve 4A, HCl / tetrahydrofuran; diethyl ether

With hydrogenchloride; 4 A molecular sieve; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; acetonitrile;

upstream raw materials:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

benzyl bromide

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

benzaldehyde dimethyl acetal

Downstream raw materials:

tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-<(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1->3)>-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside

tert-butyldimethylsilyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>4)-2-azido-6-O-benzyl-2-deoxy-β-D-glucopyranoside