(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

Base Information

Chemical Name:(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane
CAS No.:176168-13-1
Molecular Formula:C₃₁H₄₆OSSi
Molecular Weight:494.857
Hs Code.:

(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

Synonyms:(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

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Chemical Property of (1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

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Technology Process of (1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

There total 12 articles about (1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane 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: 89.0%

: N-(Phenylsulfenyl)succinimide

: 176168-12-0
(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-(hydroxymethyl)cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

: 176168-13-1
(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

Guidance literature:: With tributylphosphine; In benzene;
DOI:10.1039/cc9960000325

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 176168-13-1
(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, RT, 45 min

2: PCC, NaOAc, silica / CH₂Cl₂ / 4 h / 0 - 20 °C

3: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, from 0 deg C to RT, 2 h

4: 63 percent / LiTi(Oi-Pr)4(SPh) / tetrahydrofuran; hexane / 72 h / Ambient temperature

5: 91 percent / DIBAL-H / hexane; CH₂Cl₂ / 4 h / -78 °C

6: 90 percent / chiral dioxaborolane catalyst / CH₂Cl₂; hexane / 168 h / -40 °C

7: 1.) n-Bu₃P / 1.) benzene, RT, 10 min, 2.) benzene, RT, 1.5 h

With tributylphosphine; LiTi(Oi-Pr)4(SPh); chiral dioxaborolane catalyst; sodium acetate; silica gel; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja960964j

Reference yield:

: 163015-20-1
(1R,3S,4S,6R)-1,6-bis-<3-hydroxy-1(E)-propen-1-yl>bicyclopropane

: 176168-13-1
(1R,3S,4R,6S,7S,9R,10S,12R)-1-<<(tert-butyldimethylsilyl)oxy>methyl>-12-<2-<(1S,2R)-2-<(phenylthio)methyl>cyclopropyl>-1(E)-ethen-1-yl>quatercyclopropane

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / chiral dioxaborolane catalyst / CH₂Cl₂ / 40 h / Ambient temperature

2: 1.) NaH / 1.) THF, RT, 45 min, 2.) THF, RT, 45 min

3: PCC, NaOAc, silica / CH₂Cl₂ / 4 h / 0 - 20 °C

4: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, from 0 deg C to RT, 2 h

5: 63 percent / LiTi(Oi-Pr)4(SPh) / tetrahydrofuran; hexane / 72 h / Ambient temperature

6: 91 percent / DIBAL-H / hexane; CH₂Cl₂ / 4 h / -78 °C

7: 90 percent / chiral dioxaborolane catalyst / CH₂Cl₂; hexane / 168 h / -40 °C

8: 1.) n-Bu₃P / 1.) benzene, RT, 10 min, 2.) benzene, RT, 1.5 h

With tributylphosphine; LiTi(Oi-Pr)4(SPh); chiral dioxaborolane catalyst; sodium acetate; silica gel; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja960964j