(2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol
• CAS No.: 130277-18-8
• Molecular Formula: C₃₂H₄₅N₃O₅S
• Molecular Weight: 583.792

Synonyms:(2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol

Chemical Property of (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol

There total 1 articles about (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol 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: 92.0%

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol (103348-50-1) + p-toluenesulfonyl chloride (98-59-9) → (2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol (130277-18-8)

Guidance literature:

With triethylamine; In chloroform; for 24h; Ambient temperature;

DOI:10.1016/S0008-6215(00)90529-9

Reference yield: 73.0%

(2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol (130277-18-8) + potassium thioacetate (10387-40-3) → (2R,3R,4E)-1-Acetylthio-2-azido-3-benzoyloxy-4-octadecene (130296-11-6)

Guidance literature:

In ethanol; toluene; for 2h; Ambient temperature;

Reference yield:

(2S,3R,4E)-2-azido-3-O-benzoyl-1-O-(p-tolylsulfonyl)-4-octadecene-1,3-diol (130277-18-8) → Benzoic acid (E)-(R)-1-[(R)-1-amino-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl]-hexadec-2-enyl ester (136591-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) acetic anhydride, pyridine / 1.) DMF, 24 h, 40 deg C, 2.) overnight, r.t.

2: H₂S, pyridine / H₂O / 48 h / Ambient temperature

With pyridine; hydrogen sulfide; acetic anhydride; In water;

DOI:10.1016/S0008-6215(00)90529-9

upstream raw materials:

(2S,3R,4E)-2-azido-3-benzoyloxy-4-octadecen-1-ol

p-toluenesulfonyl chloride

Downstream raw materials:

(2R,3R,4E)-1-Acetylthio-2-azido-3-benzoyloxy-4-octadecene

Benzoic acid (E)-(R)-1-{(R)-1-amino-2-[(2S,3R,4S,5R,6R)-3,4-diacetoxy-6-acetoxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ylsulfanyl]-ethyl}-hexadec-2-enyl ester

O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->1)-(2R,3R,4E)-3-benzoyloxy-2-octadecanamido-4-octadecene-1-thiol

Benzoic acid (E)-(R)-1-[(R)-1-amino-2-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-ylsulfanyl)-ethyl]-hexadec-2-enyl ester

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