(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

Base Information

Chemical Name:(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol
CAS No.:1384463-70-0
Molecular Formula:C₃₀H₃₈O₄Si
Molecular Weight:490.715
Hs Code.:

Synonyms:(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

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Chemical Property of (3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

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Technology Process of (3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

There total 6 articles about (3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-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: 68.0%

: tert-butyl(2-((4R,5S)-2-(4-methoxyphenyl)-5-vinyl-1,3-dioxolan-4-yl)ethoxy)diphenylsilane

: 1384463-70-0
(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

: (3S,4R)-6-(tert-butyldiphenylsilyloxy)-4-(4-methoxybenzyloxy)hex-1-en-3-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 2h; regioselective reaction;
DOI:10.1016/j.tetlet.2016.10.068

Reference yield:

: 1384463-72-2
(R)-3-(tert-butyldiphenylsilyloxy)-1-((S)-oxiran-2-yl) propan-1-ol

: 1384463-70-0
(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 °C / Inert atmosphere

1.2: 3 h / -20 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 20 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; mineral oil;
DOI:10.1016/j.tetasy.2012.04.019

Reference yield:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 1384463-70-0
(3R,4S)-1-(tert-butyldiphenylsilyloxy)-4-(4-methoxy-benzyl-oxy)hex-5-en-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: copper(l) iodide / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere

1.2: 2 h / -20 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -25 °C / Inert atmosphere; Molecular sieve

2.2: 12 h / -25 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -20 °C / Inert atmosphere

3.2: 3 h / -20 - 20 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.75 h / 0 - 20 °C / Inert atmosphere

4.2: 4 h / 0 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; copper(l) iodide; n-butyllithium; L-(+)-diisopropyl tartrate; sodium hydride; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 1.2: Grignard reaction / 1.3: Grignard reaction / 2.1: Sharpless epoxidation / 2.2: Sharpless epoxidation;
DOI:10.1016/j.tetasy.2012.04.019