6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

Base Information

• Chemical Name: 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside
• CAS No.: 236115-70-1
• Molecular Formula: C₃₃H₃₃N₃O₄S
• Molecular Weight: 567.709
• Mol file: 236115-70-1.mol

Synonyms:6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

Chemical Property of 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside

There total 3 articles about 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-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: 57.0%

benzyl bromide (100-39-0) + 6-azido-6-deoxy-1-phenylthio-β-D-glucopyranoside (236115-72-3) → 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside (236115-70-1)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4.5h;

DOI:10.1021/ja9910356

Reference yield:

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-62-0,77481-63-1,105088-17-3,149495-84-1) → 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside (236115-70-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / pyridine / 20 h / 0 - 20 °C

2: 90 percent / NaN₃ / dimethylformamide / 5 h / 80 °C

3: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 °C

With pyridine; sodium azide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/ja9910356

Reference yield:

6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside (236115-71-2) → 6-azido-6-deoxy-2,3,4-tri-O-benzyl-1-phenylthio-β-D-glucopyranoside (236115-70-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaN₃ / dimethylformamide / 5 h / 80 °C

2: 57 percent / NaH / dimethylformamide / 4.5 h / 0 - 20 °C

With sodium azide; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/ja9910356

upstream raw materials:

benzyl bromide

6-azido-6-deoxy-1-phenylthio-β-D-glucopyranoside

(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

6-(4-methylbenzenesulfonate)-phenyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

(1S,2S,4S,5S)-1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-4-O-(6''-azido-6''-deoxy-2'',3'',4''-tri-O-benzyl-α-D-glucopyranosyl)-2,5-diazido-cyclohexane-1,4-diol

C₆₀H₆₄N₁₂O₁₀

1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-L-glucopyranosyl)-3-O-(6''-azido-6''-deoxy-2'',3'',4''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol

1-O-(6'-azido-6'-deoxy-2',3',4'-tri-O-benzyl-α-D-glucopyranosyl)-3-O-(6''-azido-6''-deoxy-2'',3'',4''-tri-O-benzyl-α-D-glucopyranosyl)-4,6-diazido-cyclohexan-1,2,3-ol