(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol
CAS No.:213777-21-0
Molecular Formula:C₃₁H₄₈O₅Si
Molecular Weight:528.805
Hs Code.:

Synonyms:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

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Chemical Property of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

Chemical Property:

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Technology Process of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

There total 3 articles about (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-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: 95.0%

: 64-17-5
ethanol

: 213777-20-9
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5,5-bis(isopropyloxy)pent-2-enyl]-1,4-di-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-21-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

Guidance literature:: With hydrogen; palladium on activated charcoal; for 4h;
DOI:10.1016/S0040-4039(98)01290-8

Reference yield:

: 213777-18-5
(1S,2S,3R,4R)-1,4-Bis(triethylsilyloxy)-3-(methoxycarbonylmethyl)-2-tert-butyldiphenylsilyloxymethylcyclopentane

: 213777-21-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 93 percent / DIBAL-H / toluene / 0.5 h / -78 °C

2.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

2.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

3.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

With hydrogen; sodium hexamethyldisilazane; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; toluene; 2.2: Wittig reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

: 213777-19-6
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol

: 213777-21-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(5,5-diethoxypentyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaN(SiMe₃)2 / tetrahydrofuran / 2 h / -80 °C

1.2: 83 percent / tetrahydrofuran / 2 h / -80 - 20 °C

2.1: 95 percent / H₂ / Pd/C / 4 h / 2068.65 Torr

With hydrogen; sodium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1.2: Wittig reaction;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6