BOC-THR-OBZL

Base Information

• Chemical Name: BOC-THR-OBZL
• CAS No.: 33662-26-9
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 33662-26-9.mol

Synonyms:(2S)-2-<(tert-butoxycarbonyl)amino>-3,3-dimethyl-1-butanol;2-tert-butoxycarbonylamino-3-hydroxy-butyric acid benzyl ester;(S)-[1-(hydroxymethyl)-2,2-dimethylpropyl]carbamic acid 1,1-dimethylethyl ester;N-Boc-L-threonine benzyl ether;N-Boc-L-tert-leucinol;N-Boc-Thr-OBn;Boc-Thr-OBn;(S)-2-N-<(1,1-dimethylethoxy)carbonyl>amino-3,3-dimethylbutanol;(1-hydroxymethyl-2,2-dimethylpropyl)-carbamic acid tert-butyl ester;N-Boc-L-threonine benzyl ester;(S)-(-)-N-Boc-tert-leucinol;tert-butyl N-[(1S)-1-(hydroxymethyl)-2,2-dimethylpropyl]carbamate;N-Boc-(S)-(+)-tert-leucinol;(2S,3R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-hydroxybutanoate;

Chemical Property of BOC-THR-OBZL

Chemical Property:

• PSA: 84.86000
• LogP: 2.39480
• Storage Temp.: 2-8°C

Purity/Quality:

98.5% ^*data from raw suppliers

Boc-L-Thr-OBzl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Boc-Thr-Obzl is used in preparation of of substituted Oxopyridine derivatives as factor XIa and plasma kallikrein inhibitors useful in treating Thrombotic or Thromboembolic diseases.

Technology Process of BOC-THR-OBZL

There total 10 articles about BOC-THR-OBZL 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: 100.0%

Boc-Thr-OH (2592-18-9) + benzyl bromide (100-39-0) → N-(tert-butyloxycarbonyl)-threonine benzyl ester (140422-54-4,33662-26-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 0 - 23 ℃; for 15h; Inert atmosphere;

DOI:10.1021/ja502744a

Reference yield: 98.0%

C35H35NO5 → N-(tert-butyloxycarbonyl)-threonine benzyl ester (140422-54-4,33662-26-9)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1021/acs.joc.9b02809

Reference yield: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3R)-threonine benzyl ester (33640-67-4) → N-(tert-butyloxycarbonyl)-threonine benzyl ester (140422-54-4,33662-26-9)

Guidance literature:

With sodium hydrogencarbonate; In methanol; water; at 0 - 20 ℃; for 12h; Inert atmosphere;

upstream raw materials:

Boc-Thr-OH

benzyl chloride

benzyl bromide

Boc-L-allo threonine dicyclohexylamine

Downstream raw materials:

(2S,3R)-threonine benzyl ester

(2S,3R)-3-Acetoxy-2-tert-butoxycarbonylamino-butyric acid benzyl ester

benzyl (Z)-2-((tert-butoxycarbonyl)amino)but-2-enoate

Refernces

• 1、 Ding, Pingyu,Duncton, Matthew A. J.,Fan, Dazhong,Gordon, Eric M.,Grygorash, Ruslan,Li, Xianfeng,Low, Eddy,Ni, Zhi-Jie,Qi, Longwu,Sun, Jiawei,Wang, Brian J.,Yu, Guijun. "Toward Orally Absorbed Prodrugs of the Antibiotic Aztreonam. Design of Novel Prodrugs of Sulfate Containing Drugs. Part 2". supporting information. p. 162 - 165. Retrieved 2020/01/31.
• 2、 Soley, Jacob,Taylor, Scott D.. "Mild, Rapid, and Chemoselective Procedure for the Introduction of the 9-Phenyl-9-fluorenyl Protecting Group into Amines, Acids, Alcohols, Sulfonamides, Amides, and Thiols". . . Retrieved 2020/02/04.