(R)-tert-Butyl 2-amino-4-methylpentanoate

Base Information

• Chemical Name: (R)-tert-Butyl 2-amino-4-methylpentanoate
• CAS No.: 67617-35-0
• Molecular Formula: C10H21 N O2
• Molecular Weight: 187.282
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID50427400
• Nikkaji Number: J2.820.999A
• Wikidata: Q72487341
• Mol file: 67617-35-0.mol

Synonyms:(R)-tert-Butyl 2-amino-4-methylpentanoate;67617-35-0;tert-butyl (2R)-2-amino-4-methylpentanoate;D-Leucine tert-butyl ester;H-D-LEU-OTBU HCL;Tert-butyl D-leucinate;d-leucine t-butyl ester;SCHEMBL2541315;DTXSID50427400;HBEJJYHFTZDAHZ-MRVPVSSYSA-N;MFCD10568783;AKOS017438981;FD21899;BS-24440;CS-0454850;EN300-148439;(R)-tert-Butyl 2-amino-4-methylpentanoate (H-D-Leu-OtBu)

Chemical Property of (R)-tert-Butyl 2-amino-4-methylpentanoate

Chemical Property:

• PSA: 52.32000
• LogP: 2.40180
• Storage Temp.: 0-6°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 187.157228913
• Heavy Atom Count: 13
• Complexity: 170

Purity/Quality:

99% ^*data from raw suppliers

H-D-Leu-OtBu*HCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(C(=O)OC(C)(C)C)N
• Isomeric SMILES: CC(C)C[C@H](C(=O)OC(C)(C)C)N

Technology Process of (R)-tert-Butyl 2-amino-4-methylpentanoate

There total 4 articles about (R)-tert-Butyl 2-amino-4-methylpentanoate 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%

tert-butyl (R)-2-amino-4-methylpent-4-enoate (339304-38-0) + (2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester (611182-64-0) → leucine tert-butylester (17389-05-8) + D-leucine t-butyl ester (67617-35-0) + 2-[2-hydroxy-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid tert-butyl ester + HO-D-Hpla(TIPS)-D-Leu-O-t-Bu (611182-65-1)

Guidance literature:

tert-butyl (R)-2-amino-4-methylpent-4-enoate; (2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester; In tetrahydrofuran; at 20 ℃; for 24h;

With palladium on activated charcoal; hydrogen; In tetrahydrofuran; for 24h;

DOI:10.1021/ja037290e

Reference yield: 61.0%

tert-butyl 4-methyl-2-oxopentanoate (75716-87-9) → D-leucine t-butyl ester (67617-35-0)

Guidance literature:

tert-butyl 4-methyl-2-oxopentanoate; With C₄₃H₅₅N₃O₃S; 2-CHLOROBENZYLAMINE; In benzene; at 50 ℃; for 60h; Molecular sieve; Inert atmosphere; Schlenk technique;

With hydrogenchloride; In tetrahydrofuran; benzene; enantioselective reaction;

DOI:10.1021/ol302427d

Reference yield:

tert-butyl 4-methyl-2-oxopentanoate (75716-87-9) → L-leucine tert-butyl ester (21691-53-2) + D-leucine t-butyl ester (67617-35-0)

Guidance literature:

tert-butyl 4-methyl-2-oxopentanoate; With p-nitrobenzylamine; C₅₀H₃₄F₆NO₂⁽¹⁺⁾*C₁₀H₁₁O₂^(1-); In 1,3,5-trimethyl-benzene; at 10 ℃; for 72h; Molecular sieve;

With hydrogenchloride; In tetrahydrofuran; water; 1,3,5-trimethyl-benzene; at 0 ℃; for 1h; enantioselective reaction;

DOI:10.1021/acs.orglett.9b00588

upstream raw materials:

tert-butyl (R)-2-amino-4-methylpent-4-enoate

(2R,3S)-3-[4-(triisopropylsilanyloxy)phenyl]oxirane-2-carboperoxoic acid tert-butyl ester

tert-butyl 4-methyl-2-oxopentanoate

Downstream raw materials:

C₂₆H₂₉N₃O₃

2-[7-(3,5-dimethoxy-benzylamino)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-4-methyl-pentanoic acid benzyloxy-amide

tert-butyl (2R)-2-[7-[(3,5-dimethoxybenzyl)oxy]-1,1-dioxido-4,5-dihydro-1,2,5-benzothiadiazepin-2(3H)-yl]-4-methylpentanoate

2-[7-(3,5-dimethoxy-benzylamino)-1,1-dioxo-1,3,4,5-tetrahydro-1λ⁶-benzo[f][1,2,5]thiadiazepin-2-yl]-4-methyl-pentanoic acid

Refernces

• 1、 Xiao, Xiao,Liu, Mao,Rong, Chao,Xue, Fazhen,Li, Songlei,Xie, Ying,Shi, Yian. "An efficient asymmetric biomimetic transamination of α-keto esters to chiral α-amino esters". supporting information. p. 5270 - 5273. Retrieved 2013/01/15.
• 2、 Studer,Lergier,Lanz,Boehni,Vogler. "Syntheses in the polymyxin series. 10. Synthesis of colistin A (polymyxin E-1)". . p. 1371 - 1378. Retrieved 2007/10/07.