(Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol

Base Information

• Chemical Name: (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol
• CAS No.: 444804-70-0
• Molecular Formula: C₄₃H₆₀O₄Si₃
• Molecular Weight: 725.203

Synonyms:(Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol

Chemical Property of (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol

Chemical Property:

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Technology Process of (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol

There total 2 articles about (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-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: 33.0%

(Z)-<(trimethylsilyl)propenyl>magnesium bromide (93423-80-4) + 3,5-bis-O-(tert-butyldiphenylsilyl)-2-deoxy-D-ribofuranose → (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol (444804-70-0) + (Z)-(2R,3S,5R)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol

Guidance literature:

In diethyl ether; at 0 ℃; for 16h;

DOI:10.1016/S0040-4020(02)00049-2

Reference yield:

trimethyl(prop-1-ynyl)silane (6224-91-5) → (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol (444804-70-0)

Guidance literature:

Multi-step reaction with 2 steps

1: isobutylmagnesium bromide; Cp₂TiCl₂ / diethyl ether / 6 h / 40 °C

2: 33 percent / diethyl ether / 16 h / 0 °C

With bis(cyclopentadienyl)titanium dichloride; isobutylmagnesium bromide; In diethyl ether;

DOI:10.1016/S0040-4020(02)00049-2

Reference yield: 91.0%

bis(trichloromethyl) carbonate (32315-10-9) + (Z)-(2R,3S,5S)-1,3-bis-(tert-butyldiphenylsilyloxy)-6-trimethylsilyl-oct-6-ene-2,5-diol (444804-70-0) → (4R,5S,7S)-5-tert-butyldiphenylsilyloxy-4-tert-butyldiphenylsilyloxymethyl-7-[(Z)-1-trimethylsilyl-prop-1-enyl]-[1,3]dioxepan-2-one (444804-85-7)

Guidance literature:

With pyridine; 4 A molecular sieve; triethylamine; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1039/b000299m

upstream raw materials:

(Z)-<(trimethylsilyl)propenyl>magnesium bromide

trimethyl(prop-1-ynyl)silane

Downstream raw materials:

(4R,5S,7S)-5-tert-butyldiphenylsilyloxy-4-tert-butyldiphenylsilyloxymethyl-7-[(Z)-1-trimethylsilyl-prop-1-enyl]-[1,3]dioxepan-2-one

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