5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 882167-03-5
• Molecular Formula: C₃₇H₄₆N₄O₈S
• Molecular Weight: 706.86
• Mol file: 882167-03-5.mol

Synonyms:5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 2 articles about 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-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:

n-Pent-4-enyl alcohol (821-09-0) → 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

2: 95 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja057584v

Reference yield:

O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate (135415-92-8) → 5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

2: 95 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

With 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja057584v

Reference yield: 88.0%

5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-03-5) → {2-[5-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1-sulfonyl]-ethyl}-carbamic acid benzyl ester (882167-04-6)

Guidance literature:

5-[2-(benzyloxycarbonylamino)-1-thioethyl]-pentyl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside; With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; at 20 ℃; for 16h;

With potassium hydroxide; In methanol; at 20 ℃; for 16h;

With potassium peroxomonosulfate; In methanol; at 0 ℃; for 1.5h;

DOI:10.1021/ja057584v

upstream raw materials:

n-Pent-4-enyl alcohol

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

Downstream raw materials:

{2-[5-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1-sulfonyl]-ethyl}-carbamic acid benzyl ester

{2-[5-((2R,3R,4R,5S,6R)-3-Amino-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1-sulfonyl]-ethyl}-carbamic acid benzyl ester