Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester
• CAS No.: 185681-39-4
• Molecular Formula: C₂₂H₂₈O₈S₂
• Molecular Weight: 484.592

Synonyms:Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

Chemical Property of Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

There total 2 articles about Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl 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: 95.0%

methanesulfonyl chloride (124-63-0) + 4,6-di-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol (185681-38-3) → Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester (185681-39-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1002/jlac.199619961219

Reference yield:

3,5-di-O-benzyl-D-xylofuranose (16054-77-6,120693-82-5,120693-83-6) → Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester (185681-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / BuLi / hexane; tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 6 h

2: 95 percent / Et₃N, DMAP / CH₂Cl₂ / 12 h / Ambient temperature

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/jlac.199619961219

Reference yield: 96.0%

Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester (185681-39-4) → (2R,3R,4E)-6-bromo-1,3-di-O-benzyl-2-O-methylsulphonyl-4-hexene-1,2,3-triol

Guidance literature:

With copper(l) cyanide; magnesium bromide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/jo005602f

upstream raw materials:

methanesulfonyl chloride

4,6-di-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol

3,5-di-O-benzyl-D-xylofuranose

Downstream raw materials:

(2R,3R,4E)-1,3-Di-O-benzyl-2-O-methylsulfonyloctadec-4-ene-1,2,3-triol

Methanesulfonic acid (3E,7E)-(1R,2R)-2-benzyloxy-1-benzyloxymethyl-8-methyl-heptadeca-3,7-dienyl ester

(2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

(2R,3R,4E,8E)-1,3-di-O-benzyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

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