(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Base Information

Chemical Name:(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester
CAS No.:104464-22-4
Molecular Formula:C₁₂H₁₆O₇
Molecular Weight:272.255
Hs Code.:

Synonyms:(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Chemical Property of (3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

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Technology Process of (3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

There total 5 articles about (3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl 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:

: 104464-09-7
(3R,4S,6S)-3,4-Diacetoxy-6-((S)-2-methyl-1-phenyl-propoxy)-cyclohex-1-enecarboxylic acid methyl ester

: 104464-22-4
(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; Yield given; 1.) 0 deg C; 2.) room temperature, 4 h and 20 min;
DOI:10.1021/ja00283a036

Reference yield:

: 104464-04-2
(1S,4R,8S)-8-((S)-2-Methyl-1-phenyl-propoxy)-4-(toluene-4-sulfonyl)-2-oxa-bicyclo[2.2.2]oct-5-en-3-one

: 104464-22-4
(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / methanol; CH₂Cl₂ / 0.08 h / -78 °C

2: 1.) aluminum amalgam; 2.) p-nitroperbenzoic acid / 1.) reflux; 2.) 0 deg C, chloroform, room temperature, 16 h

3: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

4: 100 percent / DMAP, triethylamine / CH₂Cl₂ / 1.) 0 deg C; 2.) room temperature, 1 h

5: trifluoroacetic acid / CH₂Cl₂ / 1.) 0 deg C; 2.) room temperature, 4 h and 20 min

With 4-nitroperbenzoic acid; dmap; aluminium amalgam; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ja00283a036

Reference yield:

: (1R,3S,5S,6S)-5-Hydroxy-3-((S)-2-methyl-1-phenyl-propoxy)-7-oxa-bicyclo[4.1.0]heptane-2-carboxylic acid methyl ester

: 104464-22-4
(3R,4S,6S)-3,4-Diacetoxy-6-hydroxy-cyclohex-1-enecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: DBU / CH₂Cl₂ / -78 deg C, 5 min, room temperature, 2.5 h

2: 100 percent / DMAP, triethylamine / CH₂Cl₂ / 1.) 0 deg C; 2.) room temperature, 1 h

3: trifluoroacetic acid / CH₂Cl₂ / 1.) 0 deg C; 2.) room temperature, 4 h and 20 min

With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1021/ja00283a036