(3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate

Base Information

• Chemical Name: (3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate
• CAS No.: 135383-55-0
• Molecular Formula: C₂₀H₃₁NO₅
• Molecular Weight: 365.47
• European Community (EC) Number: 808-978-8
• Mol file: 135383-55-0.mol

Synonyms:135383-55-0;(3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate;(3R,4S,5S)-tert-butyl4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate;Monomethyl auristatin E intermediate-7;tert-butyl (3R,4S,5S)-3-hydroxy-5-methyl-4-(phenylmethoxycarbonylamino)heptanoate;MFCD28386970;AZTSBAWJROLRIQ-LESCRADOSA-N;AKOS037650990;CS-15654;HY-78901;CS-0009818;D72199;(3R,4S,5S)-t-Butyl 4-(((benZyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate

Chemical Property of (3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate

Chemical Property:

• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 365.22022309
• Heavy Atom Count: 26
• Complexity: 440

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCC(C)C(C(CC(=O)OC(C)(C)C)O)NC(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)OC(C)(C)C)O)NC(=O)OCC1=CC=CC=C1

Technology Process of (3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate

There total 7 articles about (3R,4S,5S)-tert-butyl 4-(((benzyloxy)carbonyl)amino)-3-hydroxy-5-methylheptanoate 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: 90.0%

(4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester (135383-54-9) → (3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester (135383-55-0)

Guidance literature:

With sodium tetrahydroborate; In methanol;

DOI:10.1016/S0040-4039(00)79932-1

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → (3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester (135383-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 5.5 h / Ambient temperature

2: tetrahydrofuran

In tetrahydrofuran;

DOI:10.1248/cpb.43.1706

Reference yield:

t-butyl lithioacetate (150942-98-6) → (3R,4S,5S)-4-Benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid tert-butyl ester (135383-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) CDI / 1) THF

2: 90 percent / NaBH₄ / methanol

With sodium tetrahydroborate; 1,1'-carbonyldiimidazole; In methanol;

DOI:10.1016/S0040-4039(00)79932-1

upstream raw materials:

(4S,5S)-4-Benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid tert-butyl ester

t-butyl lithioacetate

N-Cbz-L-Isoleucine

acetic acid tert-butyl ester

Downstream raw materials:

Boc-(S)-Val-(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

dolastatin 10

Cbz-Dil-Dap-Doe

(3R,4S,5S)-Dil-(2R,3R,4S)-Dap-(S)-Doe

Refernces

• 1、 Miyazaki,Kobayashi,Natsume,Gondo,Mikami,Sakakibara,Tsukagoshi. "Synthesis and antitumor activity of novel dolastatin 10 analogs". . p. 1706 - 1718. Retrieved 2007/10/03.