(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

Base Information

Chemical Name:(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate
CAS No.:1392307-81-1
Molecular Formula:C₁₁H₁₈O₄
Molecular Weight:214.262
Hs Code.:

Synonyms:(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

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Chemical Property of (1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

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Technology Process of (1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

There total 17 articles about (1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate 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: 91.0%

: 1392307-76-4
(1S,2R,3R,4R,5R)-methyl 3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarboxylate

: 1392307-81-1
(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

Guidance literature:: (1S,2R,3R,4R,5R)-methyl 3-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-5-methyl-2-vinylcyclohexanecarboxylate; With boron tribromide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 96h;
DOI:10.1002/anie.201108223

Reference yield:

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1392307-81-1
(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

2.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

3.1: dichloromethane / 20 h

4.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

5.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

6.2: 0.25 h

7.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: Oxone / N,N-dimethyl-formamide / 18 h / 20 °C

9.1: diethyl ether / 0 °C

10.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

10.2: 96 h / 20 °C

With pyrrolidine; Oxone; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; boron tribromide; diisobutylaluminium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Dess-Martin oxidation / 3.1: Wittig reaction / 7.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223

Reference yield:

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

: 1392307-81-1
(1S,2R,3R,4R,5R)-methyl 3,4-dihydroxy-5-methyl-2-vinylcyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2.1: dichloromethane / 20 h

3.1: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

4.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / Cooling with ice

5.2: 0.25 h

6.1: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: Oxone / N,N-dimethyl-formamide / 18 h / 20 °C

8.1: diethyl ether / 0 °C

9.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

9.2: 96 h / 20 °C

With pyrrolidine; Oxone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; boron tribromide; diisobutylaluminium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 1.1: Dess-Martin oxidation / 2.1: Wittig reaction / 6.1: Tsuji-Trost cyclization;
DOI:10.1002/anie.201108223