(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol
CAS No.:334670-37-0
Molecular Formula:C₄₄H₇₄O₅Si₃
Molecular Weight:767.325
Hs Code.:

Synonyms:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

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Chemical Property of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

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Technology Process of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

There total 2 articles about (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)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: 70.0%

: 70665-02-0
3-(2-tetrahydropyranyloxy)propyltriphenylphosphonium bromide

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

: 334670-37-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

Guidance literature:: 3-(2-tetrahydropyranyloxy)propyltriphenylphosphonium bromide; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -80 ℃; for 0.166667h;

(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-(formylmethyl)-1,4-bis-O-(triethylsilyl)cyclopentane-1,4-diol; In tetrahydrofuran; toluene; at -80 - 20 ℃; for 1h; Further stages.;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6

Reference yield:

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

: 334670-37-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: KN(SiMe₃)2 / tetrahydrofuran; toluene / 0.17 h / -80 °C

2.2: 70 percent / tetrahydrofuran; toluene / 1 h / -80 - 20 °C

With potassium hexamethylsilazane; diisobutylaluminium hydride; 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: 88.0%

: 334670-37-0
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]-1,4-bis(triethylsilyl)cyclopentane-1,4-diol

: 334670-38-1
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-3-[(Z)-5-tetrahydropyranyloxypent-2-enyl]cyclopentane-1,4-diol

Guidance literature:: With ammonium fluoride; In tetrahydrofuran; methanol; for 2h; Heating;
DOI:10.1002/1099-0690(200102)2001:4<809::AID-EJOC809>3.0.CO;2-6