3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester

Base Information

• Chemical Name: 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester
• CAS No.: 123887-01-4
• Molecular Formula: C₂₆H₃₈O₇
• Molecular Weight: 462.584

Synonyms:3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester

Chemical Property of 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester

Chemical Property:

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Technology Process of 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester

There total 2 articles about 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl 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: 82.6%

3-[(1S,3R,4S,5R)-5-Benzyloxycarbonyloxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester (123886-96-4) → 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester (123887-01-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In 1,2-dichloro-ethane; at 55 ℃; for 44h;

DOI:10.1248/cpb.36.4722

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester (123887-01-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67.9 percent / 1.) pyridine; 2.) PCC, AcONa*3H₂O / Ambient temperature; 1.) toluene, THF; 2.) CH₂Cl₂, 30 min

2: 82.6 percent / mCPBA / 1,2-dichloro-ethane / 44 h / 55 °C

With pyridine; sodium acetate; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In 1,2-dichloro-ethane;

DOI:10.1248/cpb.36.4722

Reference yield: 89.5%

3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-benzyloxycarbonyloxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester (123887-01-4) → 3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-hydroxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester (123886-97-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.36.4722

upstream raw materials:

3-[(1S,3R,4S,5R)-5-Benzyloxycarbonyloxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

benzyl chloroformate

Downstream raw materials:

3-[(1S,3R,4S,5R)-3-(2-Acetoxy-ethyl)-5-hydroxy-2,2,4-trimethyl-cyclohexyl]-propionic acid ethyl ester

ethyl 3-<5α-(2-acetoxyethyl)-3β-benzoyloxy-4,6,6-trimethylcyclohexan-1α-yl>propionate

N-methyl-2'-<(2-cyanoethyl)thio>-3-<3α-(2-methanesulfonyloxyethyl)-2,2,4-trimethyl-4-cyclohexen-1α-yl>propionanilide

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