(E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol

Base Information

• Chemical Name: (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol
• CAS No.: 202526-29-2
• Molecular Formula: C₂₅H₃₆O₃Si
• Molecular Weight: 412.645

Synonyms:(E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol

Chemical Property of (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol

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Technology Process of (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol

There total 2 articles about (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-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: 85.0%

(E)-(2R,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-oct-6-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester (202526-22-5) → (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol (202526-29-2)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

DOI:10.1021/jo971863m

Reference yield:

(E)-6-(tert-Butyl-diphenyl-silanyloxy)-hex-4-enal (202526-21-4) → (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol (202526-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / CH₂Cl₂ / -78 - 0 °C

2: 85 percent / LAH / tetrahydrofuran / 0 °C

With lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo971863m

Reference yield: 91.0%

2,2-dimethoxy-propane (77-76-9) + (E)-(2S,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-oct-6-ene-1,3-diol (202526-29-2) → tert-butyldiphenyl[(E)-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pent-2-enyloxy]silane (202526-23-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 25 ℃;

DOI:10.1021/jo971863m

upstream raw materials:

(E)-(2R,3R)-8-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-2-methyl-oct-6-enoic acid (1R,2S)-2-[benzyl-(2,4,6-trimethyl-benzenesulfonyl)-amino]-1-phenyl-propyl ester

(E)-6-(tert-Butyl-diphenyl-silanyloxy)-hex-4-enal

Downstream raw materials:

tert-butyldiphenyl[(E)-5-[(4R,5S)-2,2,5-trimethyl-1,3-dioxan-4-yl]pent-2-enyloxy]silane

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