n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 882167-02-4
• Molecular Formula: C₂₇H₃₃N₃O₆
• Molecular Weight: 495.576
• Mol file: 882167-02-4.mol

Synonyms:n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of n-penten-4-yl-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 n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 1 articles about n-penten-4-yl-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: 65.0%

n-Pent-4-enyl alcohol (821-09-0) + O-(6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α,β-D-glucopyranosyl) trichloroacetimidate (135415-92-8) → n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-02-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 0.5h;

DOI:10.1021/ja057584v

Reference yield:

n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-02-4) → {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 (882167-05-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

2.1: aq. H₂O₂; LiOH / tetrahydrofuran / 16 h / 20 °C

2.2: aq. KOH / methanol / 16 h / 20 °C

2.3: 88 percent / KHSO₅ / methanol / 1.5 h / 0 °C

3.1: 96 percent / aq. NaOH; PMe₃ / tetrahydrofuran / 3 h / 20 °C

With lithium hydroxide; sodium hydroxide; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; trimethylphosphane; In tetrahydrofuran;

DOI:10.1021/ja057584v

Reference yield:

n-penten-4-yl-6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-β-D-glucopyranoside (882167-02-4) → {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:

Multi-step reaction with 2 steps

1.1: 95 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

2.1: aq. H₂O₂; LiOH / tetrahydrofuran / 16 h / 20 °C

2.2: aq. KOH / methanol / 16 h / 20 °C

2.3: 88 percent / KHSO₅ / methanol / 1.5 h / 0 °C

With lithium hydroxide; 2,2'-azobis(isobutyronitrile); dihydrogen peroxide; In tetrahydrofuran;

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-Amino-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-Azido-4,5-bis-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-pentane-1-sulfonyl]-ethyl}-carbamic acid benzyl ester