N-benzyloxycarbonyl (S)-β-homoserine benzyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl (S)-β-homoserine benzyl ester
• CAS No.: 133565-44-3
• Molecular Formula: C₁₉H₂₁NO₅
• Molecular Weight: 343.379
• Mol file: 133565-44-3.mol

Synonyms:N-benzyloxycarbonyl (S)-β-homoserine benzyl ester

Chemical Property of N-benzyloxycarbonyl (S)-β-homoserine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyloxycarbonyl (S)-β-homoserine benzyl ester

There total 9 articles about N-benzyloxycarbonyl (S)-β-homoserine benzyl 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: 90.0%

pentafluorophenyl ester of benzyloxycarbonyl-β-benzylaspartic acid (17543-13-4) → N-benzyloxycarbonyl (S)-β-homoserine benzyl ester (133565-44-3)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 20 ℃; for 0.25h;

DOI:10.1016/j.tetlet.2007.09.124

Reference yield: 66.0%

Z-Asp(OBzl)-OH (3479-47-8) → N-benzyloxycarbonyl (S)-β-homoserine benzyl ester (133565-44-3)

Guidance literature:

Z-Asp(OBzl)-OH; With Trimethyl borate; In tetrahydrofuran; at 0 ℃; for 0.166667h;

With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo201429w

Reference yield:

(S)-3-Benzyloxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester (123640-88-0) → N-benzyloxycarbonyl (S)-β-homoserine benzyl ester (133565-44-3)

Guidance literature:

With sodium tetrahydroborate; In 1,2-dimethoxyethane; water; at -15 ℃; for 0.00833333h; Yield given;

DOI:10.1016/S0040-4039(00)92121-X

upstream raw materials:

Z-Asp(OBzl)-OH

(S)-3-Benzyloxycarbonylamino-4-isobutoxycarbonyloxy-4-oxo-butyric acid benzyl ester

pentafluorophenyl ester of benzyloxycarbonyl-β-benzylaspartic acid

(S)-benzyl 4-(1-benzo[d][1m2m3]triazol-1-yl)-3-(benzyloxycarbonylamino)-4-oxobutanoate

Downstream raw materials:

C₁₉H₂₀INO₄

N-benzyloxycarbonyl O-t-butyldiphenylsilyl (S)-β-homoserine benzyl ester

C₁₉H₂₀N₄O₄

C₂₂H₂₂N₄O₆

Refernces

• 1、 Madhu, Chilakapati,Panguluri, Nageswara Rao,Sureshbabu, Vommina V.. "Synthesis of Nα-Z protected amino alkyl triazole acids and their application to neo-glycopeptides synthesis". . p. 858 - 864. Retrieved 2014/08/05.
• 2、 Sureshbabu,Vishwanatha,Vasantha. "A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids". body text. p. 1037 - 1042. Retrieved 2010/07/06.