(3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester

Base Information

• Chemical Name: (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester
• CAS No.: 120185-83-3
• Molecular Formula: C₁₄H₂₆O₄
• Molecular Weight: 258.358
• Mol file: 120185-83-3.mol

Synonyms:(3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester

Chemical Property of (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester

There total 8 articles about (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic 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:

(5R)-7-cyclohexyl-5-hydroxy-3-oxoheptanoic acid methyl ester (120185-82-2) → (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester (120185-83-3)

Guidance literature:

With sodium tetrahydroborate; diethyl methoxy borane; at -78 ℃; Yield given;

DOI:10.1016/S0040-4039(00)82107-3

Reference yield:

7-Cyclohexyl-5-hydroxy-3-oxo-heptanoic acid methyl ester (133906-99-7) → (3S,5S)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester (120185-83-3,133906-47-5)

Guidance literature:

With titanium(IV) isopropylate; sodium tetrahydroborate; In tetrahydrofuran; at -80 ℃; for 1.5h; Yield given;

DOI:10.1021/jo00012a047

Reference yield:

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene (74590-73-1,81114-98-9,67609-52-3) → (3R,5R)-7-Cyclohexyl-3,5-dihydroxy-heptanoic acid methyl ester (120185-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / TiCl₄ / CH₂Cl₂ / 0.08 h / -78 °C

2: 1) Dess-Martin periodinane, NaHCO₃, Na₂S₂O₃; 2) dibenylammonium trifluoroacetate / 1) CH₂Cl₂, 25 deg C, 1 h, water, stirring was continued for 30 min; 2) benzene, 6 deg C, 90 min

3: Et₂BOMe, NaBH₄ / -78 °C

With sodium tetrahydroborate; diethyl methoxy borane; sodium hydrogencarbonate; Dess-Martin periodane; sodium thiosulfate; dibenzylammonium trifluoroacetate salt; titanium tetrachloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)82107-3

upstream raw materials:

(5R)-7-cyclohexyl-5-hydroxy-3-oxoheptanoic acid methyl ester

(2R)-4-cyclohexyl-1-(5-methoxycyclohexa-1,4-dienyl)butan-2-ol

1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene

(2S,4R)-2-(2-Cyclohexyl-ethyl)-4-methyl-[1,3]dioxane

Downstream raw materials:

(4R,6R)-6-(2-cyclohexylethyl)-4-hydroxytetrahydropyran-2-one