tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside
• CAS No.: 189454-60-2
• Molecular Formula: C₁₉H₃₁N₃O₆SSi
• Molecular Weight: 457.623
• Mol file: 189454-60-2.mol

Synonyms:tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside

Chemical Property of tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside

There total 4 articles about tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside 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: 65.0%

p-toluenesulfonyl chloride (98-59-9) + tert-butyldimethylsilyl 3-azido-2,3-dideoxy-β-D-ribo-hexopyranoside (189454-50-0) → tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside (189454-60-2)

Guidance literature:

With pyridine; 1.) 0 deg C, 1 h, 2.) RT, 18 h;

DOI:10.1021/jm9800752

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside (189454-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 20 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 99 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 65 percent / pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h

With pyridine; 1H-imidazole; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jm9800752

Reference yield:

4,6-di-O-acetyl-3-azido-2,3-dideoxy-D-erythro-hexopyranose → tert-butyldimethylsilyl 3-azido-2,3-dideoxy-6-O-tosyl-β-D-ribo-hexopyranoside (189454-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 20 percent / imidazole / CH₂Cl₂ / 1.) 0 deg C, 0.5 h, 2.) RT, 18 h

2: 99 percent / sodium methoxide / methanol / 1.5 h / Ambient temperature

3: 65 percent / pyridine / 1.) 0 deg C, 1 h, 2.) RT, 18 h

With pyridine; 1H-imidazole; sodium methylate; In methanol; dichloromethane;

DOI:10.1021/jm9800752

upstream raw materials:

p-toluenesulfonyl chloride

tert-butyldimethylsilyl 3-azido-2,3-dideoxy-β-D-ribo-hexopyranoside

tert-butyldimethylsilyl chloride

tert-butyldimethylsilyl 3-azido-4,6-di-O-acetyl-2,3-dideoxy-β-D-ribo-hexopyranoside

Downstream raw materials:

4-O-(3,6-diazido-2,3,6-trideoxy-4-O-azidoacetyl-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-azido-6iodo-4-O-chloroacetyl-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3,6-diazido-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin

4-O-(3-azido-6-iodo-2,3,6-trideoxy-β-D-ribo-hexopyranosyl)-4'-benzyloxycarbonyl-epipodophyllotoxin