tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside
• CAS No.: 129163-31-1
• Molecular Formula: C₅₀H₆₃N₃O₁₂Si
• Molecular Weight: 926.149
• Mol file: 129163-31-1.mol

Synonyms:tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside

Chemical Property of tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside

There total 7 articles about tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-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: 90.0%

methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside (129163-30-0) + tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid (120312-09-6) → tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside (129163-31-1)

Guidance literature:

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; copper(ll) bromide; In nitromethane; at 20 ℃; for 2h;

DOI:10.1016/0008-6215(92)85040-7

Reference yield:

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose (80738-50-7) → tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside (129163-31-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / tin(IV) chloride / 1,2-dichloro-ethane / 3 h / 0 °C

2: 90 percent / silver trifluoromethanesulfonate, tetrabutylammonium bromide, CuBr₂, molecular sieves 4A / nitromethane / 2 h / 20 °C

With 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; copper(ll) bromide; tin(IV) chloride; In nitromethane; 1,2-dichloro-ethane;

DOI:10.1016/0008-6215(92)85040-7

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → tert-butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranoside (129163-31-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / p-TsOH / acetonitrile / 20 °C

2: 79 percent / NaH / paraffin / 2 h / 20 °C

3: 84 percent / boron-triethylamine complex, AlCl₃, molecular sieves 4A / tetrahydrofuran / 20 °C

4: 90 percent / silver trifluoromethanesulfonate, tetrabutylammonium bromide, CuBr₂, molecular sieves 4A / nitromethane / 2 h / 20 °C

With aluminium trichloride; triethylamine-borane; 4 A molecular sieve; tetrabutylammomium bromide; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; copper(ll) bromide; In tetrahydrofuran; nitromethane; acetonitrile; paraffin;

DOI:10.1016/0008-6215(92)85040-7

upstream raw materials:

methyl 3,6-di-O-acetyl-2,6-di-O-benzyl-1-thio-α-D-mannopyranoside

tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

benzaldehyde dimethyl acetal

1,3,6-tri-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranose

Downstream raw materials:

2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(3,6-di-O-acetyl-2,4-di-O-benzyl-α-D-mannopyranosyl)-D-glucopyranosyl fluoride