Pentanedioic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl methyl ester, (R)-

Base Information

• Chemical Name: Pentanedioic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl methyl ester, (R)-
• CAS No.: 83436-44-6
• Molecular Formula: C18H25NO6
• Molecular Weight: 351.4
• Mol file: 83436-44-6.mol

Synonyms:

Chemical Property of Pentanedioic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl methyl ester, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pentanedioic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl methyl ester, (R)-

There total 4 articles about Pentanedioic acid, 3-[[(phenylmethoxy)carbonyl]amino]-, 1,1-dimethylethyl methyl ester, (R)- 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: 88.0%

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid (77856-52-1) + isobutene (115-11-7,15220-85-6) → Z-β-homo-Asp(OBut)-OMe (83436-44-6)

Guidance literature:

With sulfuric acid;

DOI:10.1021/ja00387a060

Reference yield:

Z-D(tBu)-OH (5545-52-8) → Z-β-homo-Asp(OBut)-OMe (83436-44-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: isobutyl chloroformate; N-methylmorpholine / tetrahydrofuran

1.2: diethyl ether

2.1: TEA / silver benzoate

With 4-methyl-morpholine; TEA; isobutyl chloroformate; silver benzoate; In tetrahydrofuran; 2.1: Arndt-Eistert rearrangement;

DOI:10.1016/j.tetlet.2007.03.066

Reference yield:

methanol (67-56-1) + Z-Asp(OBut)-CHN2 (118248-02-5) → Z-β-homo-Asp(OBut)-OMe (83436-44-6)

Guidance literature:

With silver benzoate; triethylamine; for 30h; Ambient temperature;

DOI:10.1021/jm00123a003

upstream raw materials:

methanol

Z-Asp(OBut)-CHN₂

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid

isobutene

Downstream raw materials:

(3R)-3-benzyloxycarbonylamino-4-tert-butyoxycarbonylbutyric acid

Boc-Trp-Leu-β-homo-Asp(OBut)-NHCH2C6H5

Boc-Trp-Leu-β-homo-Asp(OBut)-NHCH2CH2C6H5

Boc-Trp-Leu-β-homo-Asp(OBut)-D-Phe-NH2