(1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl Ester

Base Information

• Chemical Name: (1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl Ester
• CAS No.: 138736-91-1
• Molecular Formula: C28H48O6
• Molecular Weight: 480.686
• Mol file: 138736-91-1.mol

Synonyms:(1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl Ester;(1S,2R)-3,3-DiMethoxy-1,2-cyclobutanedicarboxylic Acid 1,2-Bis[(1R,2S,5R)-5-Methyl-2-(1-Methylethyl)cyclohexyl] Ester;(1S,2R)-3,3-DiMethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthol Ester

Chemical Property of (1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl Ester

Chemical Property:

• PSA: 71.06000
• LogP: 5.61960

Purity/Quality:

97% ^*data from raw suppliers

(1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylicAcidDi-L-MentholEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl Ester

There total 3 articles about (1S,2R)-3,3-Dimethoxy-1,2-cyclobutanedicarboxylic Acid Di-L-Menthyl 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: 98.0%

1,1-dimethoxyethylene (922-69-0) + di-L-menthyl fumarate (34675-24-6) → (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (138736-91-1)

Guidance literature:

With diisobutylaluminum chloride; In toluene; at -70 ℃; diastereoselective reaction;

DOI:10.1021/op970214+

Reference yield: 91.0%

1,1-dimethoxyethylene (922-69-0) + bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)fumarate → (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (138736-91-1)

Guidance literature:

bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl)fumarate; With diethylaluminium chloride; In toluene; at -78 ℃; for 0.166667h; Inert atmosphere;

1,1-dimethoxyethylene; In toluene; for 0.166667h; Inert atmosphere;

Reference yield:

1,1-dimethoxyethylene (922-69-0) + di-L-menthyl fumarate (34675-24-6) → (1S,2R)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (138736-91-1) + (1R,2S)-3,3-Dimethoxy-cyclobutane-1,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (139012-63-8)

Guidance literature:

Product distribution; multistep reaction, diastereoselective <2+2> cycloaddition;

DOI:10.1016/0040-4039(91)85023-X

upstream raw materials:

1,1-dimethoxyethylene

di-L-menthyl fumarate

Downstream raw materials:

<(1S)-(1α,2β,3β)>-3-Hydroxy-1,2-cyclobutanedimethanol 1,2-dibenzoate ester

C₂₂H₂₄O₆

(2S-trans)-2,3-bis[(benzoyloxy)methyl]cyclobutanone

(2S,3R)-(+)-bis[hydroxymethyl]-1,1-dimethoxycyclobutane