(3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester
• CAS No.: 339160-95-1
• Molecular Formula: C₃₃H₃₇NO₅
• Molecular Weight: 527.66
• Mol file: 339160-95-1.mol

Synonyms:(3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Chemical Property of (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester

There total 2 articles about (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl 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:

acetic anhydride (108-24-7) + (3R,5R,6S)-3-Cyclohexylmethyl-2-hydroxy-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester → (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-95-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 8h;

DOI:10.1021/ja0042332

Reference yield:

(3R,5R,6S)-3-Cyclohexylmethyl-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester → (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-95-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂; toluene / 0.67 h / -78 °C

2: 0.512 g / Et₃N; DMAP / CH₂Cl₂ / 8 h / 20 °C

With dmap; diisobutylaluminium hydride; triethylamine; In dichloromethane; toluene;

DOI:10.1021/ja0042332

Reference yield: 95.0%

trimethylsilyl cyanide (7677-24-9) + (3R,5R,6S)-2-acetoxy-3-cyclohexylmethyl-5,6-diphenyl-morpholine-4-carboxylic acid benzyl ester (339160-95-1) → (3R,5R,6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester (339160-97-3)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; at -20 ℃; for 0.5h;

DOI:10.1021/ja0042332

upstream raw materials:

acetic anhydride

Downstream raw materials:

(3R,5R,6S)-2-cyano-3-cyclohexylmethyl-5,6-diphenylmorpholine-4-carboxylic acid benzyl ester

(2S,3R)-3-Amino-2-hydroxy-4-phenylbutyric acid hydrochloride

(2S,3R,5R,6S)-3-cyclohexylmethyl-5,6-diphenylmorpholine-2-carboxylic acid