1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

Base Information

Chemical Name:1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester
CAS No.:162463-07-2
Molecular Formula:C₂₀H₃₀O₄
Molecular Weight:334.456
Hs Code.:

Synonyms:1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

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Chemical Property of 1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

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Technology Process of 1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

There total 3 articles about 1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl 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: 90.0%

: 52457-01-9
3-Methylcyclohexa-1,4-diene-3-carboxylic acid

: 162463-06-1
((1S,5R,7S,8S)-3,3,8,11,11-Pentamethyl-2,4-dioxa-tricyclo[5.3.1.0^1,5]undec-8-yl)-methanol

: 162463-07-2
1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 48h; Ambient temperature;
DOI:10.1016/S0040-4039(00)78551-0

Reference yield:

: 162599-69-1
(1R,2S,5S,6R)-5,6-Dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

: 162463-07-2
1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / p-TosOH / acetone / 0.5 h / Ambient temperature

2: 99 percent / DIBAL / CH₂Cl₂ / 2 h

3: 90 percent / DCC, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

With dmap; diisobutylaluminium hydride; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In dichloromethane; acetone;
DOI:10.1016/S0040-4039(00)78551-0

Reference yield:

: (1S,5R,7R,8S)-3,3,8,11,11-Pentamethyl-2,4-dioxa-tricyclo[5.3.1.0^1,5]undecane-8-carboxylic acid methyl ester

: 162463-07-2
1-Methyl-cyclohexa-2,5-dienecarboxylic acid (1S,2S,5S,6R)-5,6-dihydroxy-2,8,8-trimethyl-bicyclo[3.2.1]oct-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / DIBAL / CH₂Cl₂ / 2 h

2: 90 percent / DCC, DMAP / CH₂Cl₂ / 48 h / Ambient temperature

With dmap; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1016/S0040-4039(00)78551-0