(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

Base Information

Chemical Name:(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol
CAS No.:119662-86-1
Molecular Formula:C₃₂H₅₄O₆Si
Molecular Weight:562.863
Hs Code.:

Synonyms:(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

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Chemical Property of (2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

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Technology Process of (2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

There total 15 articles about (2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-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: 67.0%

: 119649-98-8
(S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-(4-methoxy-benzyloxy)-butyraldehyde

: 105989-30-8
(3S,4R,5s)-4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethyl-1-heptyne

: 119662-86-1
(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

Guidance literature:: With n-butyllithium; cerium(III) chloride; 1.) THF, -78 deg C; 2.) 0.5h;
DOI:10.1016/0040-4039(88)85048-2

Reference yield:

: 1730-97-8
(S)-2-methylbutyraldehyde

: 119662-86-1
(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 53 percent / CrCl₃, LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

2: 86 percent / CH₂Cl₂ / 3 h

3: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

4: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

5: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

6: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

With chromium chloride; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; ethylmagnesium bromide; ozone; triphenylphosphine; zinc; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ja00112a006

Reference yield:

: 119650-01-0
(3S,4R,5S)-4-<(tert-butyldimethylsilyl)oxy>-3,5-dimethyl-1-heptene

: 119662-86-1
(2R,7S,8R,9S)-8-(tert-Butyl-dimethyl-silanyloxy)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-(4-methoxy-benzyloxy)-7,9-dimethyl-undec-5-yn-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) O₃, 2.) Me₂S / 1.) CH₃OH, -78 deg C, 10 min, 2.) CH₃OH, RT, 12 h

2: 1.) Zn, 2.) Ph₃P / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, 4 h

3: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 - 20 °C

4: 1.) EtMgBr / 1.) THF, ether, from 0 deg C to RT, 2.) THF, ether, -78 deg C, 15 min

With n-butyllithium; dimethylsulfide; ethylmagnesium bromide; ozone; triphenylphosphine; zinc; In tetrahydrofuran; hexane;
DOI:10.1021/ja00112a006