methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate

Base Information

• Chemical Name: methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate
• CAS No.: 153805-42-6
• Molecular Formula: C₂₁H₂₃NO₅
• Molecular Weight: 369.417
• Mol file: 153805-42-6.mol

Synonyms:methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate

Chemical Property of methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate

There total 6 articles about methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate 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: 75.0%

(2Z,4S)-4-amino-5-(benzyloxy)pent-2-enoic acid methyl ester hydrochloride + benzyl chloroformate (501-53-1,94274-21-2) → methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate (153805-42-6)

Guidance literature:

With sodium hydrogencarbonate;

DOI:10.1016/j.tetasy.2007.10.004

Reference yield: 65.0%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + ((R)-2-Benzyloxy-1-formyl-ethyl)-carbamic acid benzyl ester → methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate (153805-42-6)

Guidance literature:

With potassium hexamethylsilazane; 18-crown-6 ether; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1016/S0040-4020(01)81814-7

Reference yield:

O-benzyl-D-serine (10433-52-0,32520-12-0) → methyl (Z,4R)-4-[(benzyloxycarbonyl)amino]-5-benzyloxy-2-pentenoate (153805-42-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / 1N NaOH / dioxane; H₂O / 1 h / Ambient temperature

2: 1.) N-methyl morpholine, 2.) DMAP / 1.) CH₂Cl₂, 0 deg C, 15 min, 2.) CH₂Cl₂, 0 deg C, 30 min

3: DIBAL-H / toluene / 2 h / -78 °C

4: 65 percent / KN(TMS)2 / 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

With 4-methyl-morpholine; dmap; sodium hydroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; 18-crown-6 ether; In tetrahydrofuran; 1,4-dioxane; water; toluene;

DOI:10.1016/S0040-4020(01)81814-7

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

benzyl chloroformate

O-benzyl-D-serine

dibenzyl dicarbonate