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

Base Information

Chemical Name:(1S,2R,3S,4S)-4-(benzyloxymethyl)-2,3-(isopropylidenedioxy)cyclopentanol
CAS No.:1290137-26-6
Molecular Formula:C₁₆H₂₂O₄
Molecular Weight:278.348
Hs Code.:

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

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

There total 4 articles about (1S,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: 58.0%

: 1290137-25-5
(1S,2R,5S)-5-(benzyloxymethyl)-1,2-(isopropylidenedioxy)cyclopent-3-ene

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

Guidance literature:: (1S,2R,5S)-5-(benzyloxymethyl)-1,2-(isopropylidenedioxy)cyclopent-3-ene; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

In tetrahydrofuran; water; at 0 ℃; for 6h;
DOI:10.1002/ejoc.201001473

Reference yield:

: 1290137-24-4
(1S,2S,3S,4R)-2-(benzyloxymethyl)-3,4-(isopropylidenedioxy)cyclopentyl methanesulfonate

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

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: oxone / 6 h / 0 °C

With potassium tert-butylate; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: Hydroboration reaction;
DOI:10.1002/ejoc.201001473

Reference yield:

: 1290137-22-2
C₁₄H₁₈O₄S

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

Guidance literature:: Multi-step reaction with 4 steps

1.1: AD-mix β / water; tert-butyl alcohol / 12 h / 0 °C

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

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

4.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.2: oxone / 6 h / 0 °C

With potassium tert-butylate; toluene-4-sulfonic acid; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 4.1: Hydroboration reaction;
DOI:10.1002/ejoc.201001473