(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

Base Information

Chemical Name:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol
CAS No.:681449-39-8
Molecular Formula:C₃₆H₆₂O₄Si₃
Molecular Weight:643.142
Hs Code.:

Synonyms:(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

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Chemical Property of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

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Technology Process of (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

There total 1 articles about (1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)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: 94.0%

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

: 681449-39-8
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃; for 1h;
DOI:10.1021/jo035638i

Reference yield: 97.0%

: 98-59-9
p-toluenesulfonyl chloride

: 681449-39-8
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

: 681449-40-1
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-[2-(4-methylbenzenesulfonyloxy)ethyl]cyclopentane-1,4-diol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/jo035638i

Reference yield:

: 681449-39-8
(1S,2R,3R,4R)-2-(tert-butyldiphenylsilyloxymethyl)-1,4-bis-O-(triethylsilyl)-3-(2-hydroxyethyl)cyclopentane-1,4-diol

: 681449-46-7
(1S,2S,3R,4R)-1,4-di-O-benzoyl-3-ethyl-2-[(E)-10-(ethoxycarbonyl)-3-oxodec-1-enyl]cyclopentane-1,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / DMAP; triethylamine / CH₂Cl₂ / 2 h / 20 °C

2.1: 91 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / Heating

3.1: 82 percent / ammonium fluoride / methanol; tetrahydrofuran / 2 h / Heating

4.1: 94 percent / pyridine / 1 h / 20 °C

5.1: 97 percent / acetyl chloride; methanol / diethyl ether / 20 h / 20 °C

6.1: Dess-Martin periodinane; water / CH₂Cl₂ / 3 h / 20 °C

7.1: NaHMDS / tetrahydrofuran; toluene / 20 °C

7.2: 79 percent / tetrahydrofuran; toluene / -78 - 20 °C

With pyridine; methanol; dmap; lithium aluminium tetrahydride; ammonium fluoride; water; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; acetyl chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 6.1: Dess-Martin oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo035638i