(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

Base Information

Chemical Name:(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane
CAS No.:880766-65-4
Molecular Formula:C₂₆H₃₈O₆SSi
Molecular Weight:506.736
Hs Code.:

Synonyms:(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

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Chemical Property of (-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

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Technology Process of (-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

There total 8 articles about (-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane 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:

: 79060-23-4
(2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-en-1-ol

: 880766-65-4
(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 0.644 g / Ti(OiPr)4; molecular sieves 3 Angstroem; (+)-DIPT / cumene hydroperoxide / CH₂Cl₂ / 89 h / -40 °C

2.1: Et₃N; DMAP / CH₂Cl₂ / 10 h / 20 °C

3.1: diethyl ether / 1 h / -40 - -30 °C

3.2: 0.168 g / Et₃N / CH₂Cl₂ / 0.5 h

With titanium(IV) isopropylate; dmap; L-(+)-diisopropyl tartrate; 3 A molecular sieve; triethylamine; Cumene hydroperoxide; In diethyl ether; dichloromethane; 1.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol052943c

Reference yield:

: 81703-93-7
methyl (2E)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acrylate

: 880766-65-4
(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / DIBAL-H / tetrahydrofuran; hexane / 3.5 h / -78 °C

2.1: 0.644 g / Ti(OiPr)4; molecular sieves 3 Angstroem; (+)-DIPT / cumene hydroperoxide / CH₂Cl₂ / 89 h / -40 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 10 h / 20 °C

4.1: diethyl ether / 1 h / -40 - -30 °C

4.2: 0.168 g / Et₃N / CH₂Cl₂ / 0.5 h

With titanium(IV) isopropylate; dmap; L-(+)-diisopropyl tartrate; 3 A molecular sieve; diisobutylaluminium hydride; triethylamine; Cumene hydroperoxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Sharpless asymmetric epoxidation;
DOI:10.1021/ol052943c

Reference yield:

: tert-Butyl-[(2S,3R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethoxy]-diphenyl-silane

: 15681-48-8
lithium dimethylcuprate

: 124-63-0
methanesulfonyl chloride

: 880766-65-4
(-)-(2S,3R,4R)-1-tert-butyldiphenylsilyloxy-4,5-isopropylidenedioxy-2-mesyloxy-3-methylpentane

Guidance literature:: tert-Butyl-[(2S,3R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-oxiranylmethoxy]-diphenyl-silane; lithium dimethylcuprate; In diethyl ether; at -40 - -30 ℃; for 1h;

methanesulfonyl chloride; With triethylamine; In dichloromethane; for 0.5h;
DOI:10.1021/ol052943c