(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

Base Information

Chemical Name:(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid
CAS No.:87804-51-1
Molecular Formula:C₂₀H₃₂O₈
Molecular Weight:400.469
Hs Code.:

Synonyms:(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

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Chemical Property of (2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

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Technology Process of (2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

There total 5 articles about (2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid 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:

: 87804-50-0
(2S,3S,4R,6R)-3,4-diacetoxy-2-(l-menthyloxy)-6-furyl-2H-(3,4,5,6)-tetrahydropyran

: 87804-51-1
(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: With ozone;
DOI:10.1021/ja00361a042

Reference yield:

: 87804-49-7
(2S,3R,6R)-3-acetoxy-2-(l-menthyloxy)-6-furyl-2H-tetrahydropyran-4-one

: 87804-51-1
(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: K-Selectride / tetrahydrofuran / 1 h / -78 °C

2: 79 percent / triethylamine / (dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

3: ozone in oxygen / CH₂Cl₂; methanol / 0.07 h / -78 °C

With potassium tri-sec-butyl-borohydride; ozone; triethylamine; dmap; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00282a035

Reference yield:

: 104263-87-8
Acetic acid 1-[1-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-meth-(E)-ylidene]-2-trimethylsilanyloxy-allyl ester

: 87804-51-1
(2R,4R,5S,6S)-4,5-Diacetoxy-6-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyloxy)-tetrahydro-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 2.) triethylamine / 1.) (+)-Eu(hfc)3 / 1.) CDCl₃, room temperature, 24 h; 2.) methanol, room temperature, 2 h

2: K-Selectride / tetrahydrofuran / 1 h / -78 °C

3: 79 percent / triethylamine / (dimethylamino)pyridine / CH₂Cl₂ / 24 h / Ambient temperature

4: ozone in oxygen / CH₂Cl₂; methanol / 0.07 h / -78 °C

With potassium tri-sec-butyl-borohydride; ozone; triethylamine; dmap; tris{3-(heptafluoropropylhydroxymethylene)-(+)-camphorato}europium(III); In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja00282a035