(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

Base Information

Chemical Name:(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol
CAS No.:1403561-76-1
Molecular Formula:C₁₉H₃₂O₃Si
Molecular Weight:336.547
Hs Code.:

Synonyms:(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

Chemical Property:

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Technology Process of (1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

There total 6 articles about (1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol 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: 74.0%

: 1403561-75-0
(S)-3-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopent-3-en

: 1403561-76-1
(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

: 1403561-37-4
(1R,2S,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

Guidance literature:: (S)-3-(benzyloxymethyl)-1-tert-butyldimethylsilyloxycyclopent-3-en; With bis-(1,2-dimethylpropyl)borane; In tetrahydrofuran; at 0 ℃; for 48h;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; at 0 ℃; optical yield given as %de;
DOI:10.1002/chem.201200733

Reference yield:

: 153186-83-5
(+/-)-3-[(benzyloxy)methyl]cyclopent-3-en-1-ol

: 1403561-76-1
(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

: 1403561-37-4
(1R,2S,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

Guidance literature:: Multi-step reaction with 3 steps

1.1: vinyl acetate; pancreatin from porcine pancreas; triethylamine / acetone / 6 h / 20 °C / Enzymatic reaction

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

3.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 48 h / 0 °C

3.2: 0 °C

With 1H-imidazole; vinyl acetate; pancreatin from porcine pancreas; bis-(1,2-dimethylpropyl)borane; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;
DOI:10.1002/chem.201200733

Reference yield:

: 1403561-38-5
(R)-3-(benzyloxymethyl)cyclopent-3-enyl acetate

: 1403561-76-1
(1S,2R,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

: 1403561-37-4
(1R,2S,4R)-2-(benzyloxymethyl)-4-tert-butyldimethylsilyloxycyclopentanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: methanol; sodium hydroxide / 2 h / 20 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine; benzoic acid / diethyl ether / 16 h / 0 - 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

4.1: bis-(1,2-dimethylpropyl)borane / tetrahydrofuran / 48 h / 0 °C

4.2: 0 °C

With 1H-imidazole; methanol; di-isopropyl azodicarboxylate; bis-(1,2-dimethylpropyl)borane; triphenylphosphine; benzoic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; 2.1: Mitsunobu reaction;
DOI:10.1002/chem.201200733