(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

Base Information

Chemical Name:(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol
CAS No.:1146288-94-9
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

Synonyms:(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

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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 (1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

Chemical Property:

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Technology Process of (1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

There total 14 articles about (1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol 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: 87.0%

: 1146288-93-8
(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentyl benzoate

: 1146288-94-9
(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 6h;
DOI:10.1002/ejoc.201001473

Reference yield: 48.0%

: 1290137-26-6
(1S,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

: 1146288-94-9
(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

Guidance literature:: With di-isopropyl azodicarboxylate; triphenylphosphine; In diethyl ether; at 0 ℃; for 0.5h; Inert atmosphere;

(1S,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol; With benzoic acid; In diethyl ether; at 0 - 20 ℃; Inert atmosphere;

With sodium hydroxide; In methanol; at 20 ℃; for 6h; Inert atmosphere;
DOI:10.1002/ejoc.201001473

Reference yield:

: 1290137-23-3
(1S,2S,3S,4R)-2-(benzyloxymethyl)-3,4-dihydroxycyclopentyl methanesulfonate

: 1146288-94-9
(1R,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / acetone / 4 h / 20 °C

2.1: potassium tert-butylate / N,N-dimethyl-formamide / 1 h / Reflux

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.2: oxone / 6 h / 0 °C

4.1: di-isopropyl azodicarboxylate; triphenylphosphine / diethyl ether / 0.5 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

4.3: 6 h / 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; potassium tert-butylate; toluene-4-sulfonic acid; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; acetone; 3.1: Hydroboration reaction / 4.1: Mitsunobu reaction / 4.3: Mitsunobu reaction;
DOI:10.1002/ejoc.201001473