(4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester

Base Information

• Chemical Name: (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester
• CAS No.: 147778-58-3
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 147778-58-3.mol

Synonyms:(4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester

Chemical Property of (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester

There total 6 articles about (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic 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: 83.0%

methyl 2-lithioacetate + N-Z-D-valine pentafluorophenyl ester (325687-63-6) → (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester (147778-58-3)

Guidance literature:

In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)01409-X

Reference yield: 83.0%

lithium enolate of methyl acetate (57570-85-1) + N-Z-D-valine pentafluorophenyl ester (325687-63-6) → (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester (147778-58-3)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja010222c

Reference yield:

N-[(benzyloxy)carbonyl]-D-valine (1685-33-2) → (4R)-4-benzyloxycarbonylamino-3-oxo-hexanoic acid methyl ester (147778-58-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / EDAC*HCl; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 83 percent / tetrahydrofuran / -78 °C

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja010222c

upstream raw materials:

N-[(benzyloxy)carbonyl]-D-valine

Methyl trimethylsilyl malonate

N-Z-D-valine pentafluorophenyl ester

lithium enolate of methyl acetate

Downstream raw materials:

(3S,4R)-4-benzyloxycarbonylamino-3-hydroxyhexanoic acid methyl ester

(-)-tamandarin B

(3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)hexanoic acid methyl ester

(3S,4R)-4-benzyloxycarbonylamino-3-(triisopropylsilanyloxy)heptanoic acid