Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester
• CAS No.: 441775-34-4
• Molecular Formula: C₂₅H₃₅NO₁₀
• Molecular Weight: 509.554
• Mol file: 441775-34-4.mol

Synonyms:Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester

There total 2 articles about Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl 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: 65.0%

2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide (16741-27-8) + 5-<(benzyloxycarbonyl)amino>pentanol (87905-98-4) → Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester (441775-34-4)

Guidance literature:

With mercury(II) cyanide; In nitromethane; toluene; at 20 ℃;

DOI:10.1002/ejoc.200400239

Reference yield:

1,2,3,4-tetra-O-acetyl-L-fucopyranose (7404-35-5,17081-04-8,20853-37-6,27821-10-9,27821-11-0,30021-94-4,33947-15-8,34371-40-9,34371-41-0,35521-79-0,36807-81-5,36807-82-6,50615-78-6,51921-33-6,62182-03-0,64913-16-2,70004-81-8,84622-47-9,87303-56-8,108942-32-1,108942-33-2,109430-94-6,143394-72-3,24332-95-4) → Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester (441775-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / HBr; HOAc / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 65 percent / Hg(CN)2 / toluene; nitromethane / 20 °C

With hydrogen bromide; mercury(II) cyanide; acetic acid; In nitromethane; dichloromethane; toluene; 2: Helferich conditions;

DOI:10.1002/ejoc.200400239

Reference yield:

Acetic acid (2S,3S,4R,5R,6S)-3,5-diacetoxy-2-(5-benzyloxycarbonylamino-pentyloxy)-6-methyl-tetrahydro-pyran-4-yl ester (441775-34-4) → [5-((2S,3S,4R,5S,6S)-3,4,5-Trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-pentyl]-carbamic acid benzyl ester

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1002/ejoc.200400239

upstream raw materials:

2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide

5-<(benzyloxycarbonyl)amino>pentanol

1,2,3,4-tetra-O-acetyl-L-fucopyranose