(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

Base Information

Chemical Name:(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol
CAS No.:879873-80-0
Molecular Formula:C₂₅H₃₄O₂Si
Molecular Weight:394.629
Hs Code.:

Synonyms:(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

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Chemical Property of (S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

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Technology Process of (S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

There total 1 articles about (S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol 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: 75.0%

: 408348-31-2
(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane

: 115-11-7,15220-85-6
isobutene

: 879873-80-0
(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

Guidance literature:: isobutene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; (-)-B-methoxydiisopinocampheylborane; In diethyl ether; hexane; at -78 - 20 ℃; for 2h;

(1R,2R)-2-(tert-butyldiphenylsilyloxy)methyl-1-formylcyclopropane; In diethyl ether; hexane; at -78 ℃; for 2h;

With sodium hydroxide; dihydrogen peroxide; In diethyl ether; hexane; at 20 ℃; for 3h;
DOI:10.1021/ol052851n

Reference yield: 76.0%

: 879873-80-0
(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 879873-81-1
4-(2-[tert-butyldiphenylsilanyloxymethyl]cyclopropyl)-4-(4-methoxybenzyloxy)-2-methyl-1-butene

Guidance literature:: With toluene-4-sulfonic acid; In hexane; dichloromethane; at 20 ℃; for 24h;
DOI:10.1021/ol052851n

Reference yield:

: 879873-80-0
(S)-1-[(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-cyclopropyl]-3-methyl-but-3-en-1-ol

: 879873-93-5
{4-hydroxy-6-[2-(4-methoxybenzyloxy)-2-(2-methylcyclopropyl)ethyl]-3-methyltetrahydropyran-2-yl}acetic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 76 percent / TsOH / CH₂Cl₂; hexane / 24 h / 20 °C

2.1: 93 percent / TBAF / tetrahydrofuran / 3 h / 20 °C

3.1: 89 percent / PPh₃; CBr₄ / tetrahydrofuran / 2.5 h / 20 °C

4.1: 96 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

5.1: pyridine; O₃ / methanol / -78 °C

5.2: 96 percent / Me₂S / methanol / 4 h / -78 - 20 °C

6.1: iPr₂NEt; Bu₂BOTf / diethyl ether / 2 h / -78 °C

6.2: 93 percent / H₂O₂ / ethanol; methanol / 1 h / 20 °C / pH 7

7.1: 95 percent / Me₄NB(OAc)3H; AcOH / acetonitrile / 48 h / -20 °C

8.1: 83 percent / PPTS / CH₂Cl₂ / 5 h / 20 °C

9.1: 99 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

10.1: NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

11.1: 89 percent / iPr₂NEt; LiCl / acetonitrile / 5 h / 0 - 20 °C

12.1: 97 percent / 10-camphorsulfonic acid; H₂O / methanol / 2.5 h / 20 °C

13.1: 82 percent / NaH / tetrahydrofuran / 4 h / 20 °C

With pyridine; lithium aluminium tetrahydride; carbon tetrabromide; di-n-butylboryl trifluoromethanesulfonate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; 6.1: aldol reaction / 10.1: Dess-Martin oxidation / 11.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/ol052851n