{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

Base Information

• Chemical Name: {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
• CAS No.: 882167-04-6
• Molecular Formula: C₃₅H₄₄N₄O₉S
• Molecular Weight: 696.822
• Mol file: 882167-04-6.mol

Synonyms:{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

Chemical Property of {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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {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

There total 4 articles about {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 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: 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

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

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → {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 3 steps

1.1: 65 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -25 °C

2.1: 95 percent / AIBN / tetrahydrofuran / 12 h / 75 °C

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

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

3.3: 88 percent / KHSO₅ / methanol / 1.5 h / 0 °C

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

DOI:10.1021/ja057584v

upstream raw materials:

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

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

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