(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

Base Information

Chemical Name:(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester
CAS No.:371974-84-4
Molecular Formula:C₁₃H₂₀O₆
Molecular Weight:272.298
Hs Code.:

Synonyms:(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

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Chemical Property of (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

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Technology Process of (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

There total 3 articles about (1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester 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: 73.0%

: 106-95-6
allyl bromide

: 371974-81-1
(1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

: 371974-84-4
(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

Guidance literature:: (1S,2S,4R,5S)-4,5-Dihydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester; With di(n-butyl)tin oxide; In benzene; for 6h; Heating;

allyl bromide; a; With tetra-(n-butyl)ammonium iodide; cesium fluoride; In benzene; at 20 ℃; for 48h; Further stages.;
DOI:10.1021/jo015570b

Reference yield:

: 51096-08-3
(1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid

: 371974-84-4
(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / H₂SO₄ / 20 h / Heating

2.1: 99 percent / Et₃NO; OsCl₃; H₂O / CH₂Cl₂ / 15 h / 20 °C

3.1: Bu₂SnO / benzene / 6 h / Heating

3.2: 73 percent / Bu₄NI; CsF / benzene / 48 h / 20 °C

With osmium (III) chloride; triethylamine N-oxide; sulfuric acid; water; di(n-butyl)tin oxide; In dichloromethane; benzene; 1.1: Fischer esterification;
DOI:10.1021/jo015570b

Reference yield:

: 137492-80-9
(1S,2S)-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester

: 371974-84-4
(1S,2S,4R,5S)-4-Allyloxy-5-hydroxy-cyclohexane-1,2-dicarboxylic acid dimethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 99 percent / Et₃NO; OsCl₃; H₂O / CH₂Cl₂ / 15 h / 20 °C

2.1: Bu₂SnO / benzene / 6 h / Heating

2.2: 73 percent / Bu₄NI; CsF / benzene / 48 h / 20 °C

With osmium (III) chloride; triethylamine N-oxide; water; di(n-butyl)tin oxide; In dichloromethane; benzene;
DOI:10.1021/jo015570b