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

Base Information

• Chemical Name: dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate
• CAS No.: 338460-83-6
• Molecular Formula: C₁₆H₂₈O₆Si
• Molecular Weight: 344.48
• Mol file: 338460-83-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate 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: 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

Reference yield:

3-hydroxy-2-pyrone (496-64-0) → dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate (338460-83-6)

Guidance literature:

Multi-step reaction with 3 steps

1: cinchonine / water; isopropyl alcohol / 2 h / 0 °C

2: methanol / 0.33 h

3: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 60 °C

With 1H-imidazole; cinchonine; In methanol; water; N,N-dimethyl-formamide; isopropyl alcohol; 1: Diels-Alder reaction;

DOI:10.1016/j.carres.2011.04.011

Reference yield:

(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 → dimethyl (1S,2R,5S)-5-tert-butyldimethylsilyloxy-2-hydroxy-3-cyclohexene-1,2-dicarboxylate (338460-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 0.33 h

2: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 60 °C

With 1H-imidazole; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2011.04.011

upstream raw materials:

tert-butyldimethylsilyl chloride

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

3-hydroxy-2-pyrone

Downstream raw materials:

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

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

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

(3S,4R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-3-trimethylsilanyloxy-4-trimethylsilanyloxymethyl-cyclohexene