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

Base Information

Chemical Name:(2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol
CAS No.:256480-13-4
Molecular Formula:C₄₀H₅₄O₅S₂
Molecular Weight:678.998
Hs Code.:

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

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

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

There total 7 articles about (2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol 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: 89.0%

: 185681-39-4
Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

: C₁₉H₂₉LiS

: 256480-13-4
(2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

Guidance literature:: With CuCN*2LiCl; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/jo005602f

Reference yield:

: 185681-39-4
Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester

: 256480-12-3
(E)-3-methyl-2-dodecenyl phenyl sulphide

: 256480-13-4
(2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

Guidance literature:: (E)-3-methyl-2-dodecenyl phenyl sulphide; With n-butyllithium; In N,N,N,N,N,N-hexamethylphosphoric triamide;

Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester; In tetrahydrofuran; at 78 ℃;
DOI:10.1016/S0040-4039(99)01885-7

Reference yield:

: 7437-61-8
2-methyl-3,4-epoxy-1-butene

: 256480-13-4
(2R,3R,4E,8E)-1,3-di-O-benzyl-9-methyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

Guidance literature:: Multi-step reaction with 4 steps

1.1: magnesium / tetrahydrofuran

1.2: 8.72 g / copper(I) cyanide; dimethyl sulfide / tetrahydrofuran / 1 h / -20 °C

2.1: 98 percent / tri-n-butylphosphine / tetrahydrofuran / -20 - 20 °C

3.1: n-BuLi / hexane; hexamethylphosphoric acid triamide; tetrahydrofuran / 2 h / -78 °C

4.1: 89 percent / CuCN*2LiCl / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

With n-butyllithium; tributylphosphine; magnesium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane;
DOI:10.1021/jo005602f