(1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester
• CAS No.: 203627-51-4
• Molecular Formula: C₁₀H₁₄O₆
• Molecular Weight: 230.218
• Mol file: 203627-51-4.mol

Synonyms:(1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

Chemical Property of (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester

There total 2 articles about (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-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:

3-hydroxy-2-pyrone (496-64-0) → (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester (203627-51-4)

Guidance literature:

Multi-step reaction with 2 steps

1: cinchonine / propan-2-ol; H₂O / 0 °C

2: 78 percent / MeONa

With sodium methylate; Cinchonin; In water; isopropyl alcohol;

DOI:10.1016/S0040-4039(97)10843-7

Reference yield:

sodium methylate (124-41-4) + (S)-3-((1S,4R,5S)-4-Hydroxy-3-oxo-2-oxa-bicyclo[2.2.2]oct-7-ene-5-carbonyl)-4-phenyl-oxazolidin-2-one → (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester (203627-51-4)

Guidance literature:

In methanol; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)00032-1

Reference yield: 74.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,2R,5S)-2,5-Dihydroxy-cyclohex-3-ene-1,2-dicarboxylic acid dimethyl ester (203627-51-4) → dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate (338460-83-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 60 ℃; for 10h;

DOI:10.1016/S0040-4020(01)00032-1

upstream raw materials:

sodium methylate

3-hydroxy-2-pyrone

Downstream raw materials:

dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate

(4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenone

(1S,4S,6R)-4-tert-butyldimethylsilyloxy-6-hydroxymethyl-2-cyclohexenol

(1R,4S,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-1,6-bis-hydroxymethyl-cyclohex-2-enol