(Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 176384-40-0
• Molecular Formula: C₂₉H₃₇NO₄
• Molecular Weight: 463.617
• Mol file: 176384-40-0.mol

Synonyms:(Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property of (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 1 articles about (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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: 61.0%

(-)-8-phenylmenthol (65253-04-5) + (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid methyl ester → (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176384-40-0)

Guidance literature:

With trimethylaluminum; In tetrahydrofuran; at -60 ℃;

DOI:10.1248/cpb.44.636

Reference yield:

(Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176384-40-0) → N-((1R,2S)-3-Benzyloxy-1-hydroxymethyl-2-phenylsulfanyl-propyl)-acetamide

Guidance literature:

Multi-step reaction with 2 steps

1: LiSPH / toluene / -78 °C

2: 93 percent / LiAlH₄ / tetrahydrofuran / 0 °C

With lithium aluminium tetrahydride; lithium thiophenoxide; In tetrahydrofuran; toluene;

DOI:10.1248/cpb.44.636

Reference yield:

thiophenol (108-98-5) + (Z)-2-Acetylamino-4-benzyloxy-but-2-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176384-40-0) → (2R,3S)-2-Acetylamino-4-benzyloxy-3-phenylsulfanyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (176384-42-2)

Guidance literature:

With lithium thiophenoxide; In toluene; at -78 ℃; Yield given;

DOI:10.1248/cpb.44.636

upstream raw materials:

(-)-8-phenylmenthol

Downstream raw materials:

(2R,3S)-2-Acetylamino-4-benzyloxy-3-phenylsulfanyl-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester