(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

Base Information

Chemical Name:(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane
CAS No.:952101-26-7
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

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Chemical Property of (1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

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Technology Process of (1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

There total 3 articles about (1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane 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: 94.0%

: 952101-25-6
(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutane

: 952101-26-7
(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

Guidance literature:: (1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutane; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 4h; Further stages.;
DOI:10.1021/jo070861r

Reference yield:

: (4R,5R)-4-benzyloxy-2-methoxy-3,3-dimethyl-5-vinyltetrahydrofuran

: 952101-26-7
(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 74 percent / BF₃*OEt₂; n-butyllithium / Cp₂ZrCl₂ / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

3.1: BH₃*THF / tetrahydrofuran / 4 h / 0 - 20 °C

3.2: 94 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; borane-THF; boron trifluoride diethyl etherate; zirconocene dichloride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo070861r

Reference yield:

: 895532-66-8
(1S,3S,4R)-3-benzyloxy-2,2-dimethyl-4-vinylcyclobutanol

: 952101-26-7
(1S,3S,4S)-1-(tert-butyldimethylsilyloxy)-3-benzyloxy-2,2-dimethyl-4-(2-hydroxyethyl)cyclobutane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

2.1: BH₃*THF / tetrahydrofuran / 4 h / 0 - 20 °C

2.2: 94 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 4 h / 0 - 20 °C

With 2,6-dimethylpyridine; borane-THF; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jo070861r