Boc-allo-Ile-OH

Base Information

• Chemical Name: Boc-allo-Ile-OH
• CAS No.: 35264-07-4
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.292
• DSSTox Substance ID: DTXSID00426322
• Nikkaji Number: J991.707A
• Wikidata: Q72447777
• Mol file: 35264-07-4.mol

Synonyms:Boc-allo-Ile-OH;35264-07-4;BOC-L-allo-Isoleucine;Boc-L-alloisoleucine;L-Alloisoleucine, N-[(1,1-dimethylethoxy)carbonyl]-;(2S,3R)-3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;(tert-Butoxycarbonyl)-L-alloisoleucine;(2S,3R)-2-{[(tert-butoxy)carbonyl]amino}-3-methylpentanoic acid;BOC-alloisoleucine;Boc-allo-Ile-OH.nH2O;(2S,3R)-2-((TERT-BUTOXYCARBONYL)AMINO)-3-METHYLPENTANOIC ACID;SCHEMBL3205842;DTXSID00426322;QJCNLJWUIOIMMF-SFYZADRCSA-N;MFCD00151905;AKOS015892637;AM81864;DS-8738;FD21840;Boc-allo-Ile-OH, >=99.0% (TLC);N-(tert-Butyloxycarbonyl)-L-alloisoleucine;CS-0158737;EN300-764793;A874662;(2S,3R)-2-tert-butoxycarbonylamino-3-methyl-pentanoic acid;(2s,3r)-2-(tert-butoxycarbonylamino)-3-methylpentanoic acid

Chemical Property of Boc-allo-Ile-OH

Chemical Property:

• Melting Point: 60-64 °C
• Boiling Point: 356 °C at 760 mmHg
• PKA: 4.03±0.22(Predicted)
• Flash Point: 169.1 °C
• PSA: 75.63000
• Density: 1.061 g/cm³
• LogP: 2.40130
• Storage Temp.: Store at RT.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 257

Purity/Quality:

98%,99%, ^*data from raw suppliers

Boc-L--isoleucine ≥ 99% (HPLC) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC[C@@H](C)[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Uses: Boc-allo-Ile-OH is used to prepare substituted isoindolines as inhibitors of DPP8/9. It is also used to synthesize antifungal, cyclic depsipeptide aureobasidin A.

Technology Process of Boc-allo-Ile-OH

There total 30 articles about Boc-allo-Ile-OH 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: 99.0%

D-allo-isoleucine (1509-34-8,959215-79-3,18875-42-8) + di-tert-butyl dicarbonate (24424-99-5) → Boc-L-aIle-OH (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; for 2h; 0 deg C to r. t.;

DOI:10.1021/jo00037a012

Reference yield: 96.0%

D-alloisoleucine (1509-35-9,959215-79-3,18875-42-8) + 2-((tert-butoxycarbonyloxy)imino)-2-phenylacetonitrile → N-tert-butoxycarbonyl-D-alloisoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With triethylamine; In water; acetone; for 5h; Ambient temperature;

DOI:10.1021/jo00037a012

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2RS,3S)-2-amino-3-methylpentanoic acid (959215-79-3,18875-42-8) → N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + N-tert-butoxycarbonyl-D-alloisoleucine (13139-16-7,35264-07-4,55721-65-8,55780-90-0,116194-21-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 0 - 22 ℃; pH=9 - 10; Overall yield = 88 %; Overall yield = 0.77 g; diastereoselective reaction;

DOI:10.1039/c5ob02520f

upstream raw materials:

L-isoleucine

1-tert-butoxycarbonyloxy-6-chloro-1H-benzotriazole

tert-butyl alcohol

di-tert-butyl dicarbonate

Downstream raw materials:

{(S)-5-[(S)-2-((R)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-phenyl-propionylamino]-5-[3-(4-dimethylamino-benzoyl)-phenylcarbamoyl]-pentyl}-carbamic acid benzyl ester

Boc-D-allo-isoleucinol

Refernces

• 1、 Srinivasarao, Kondaparla,Agarwal, Pooja,Srivastava, Kumkum,Haq,Puri, Sunil K.,Katti. "Design, synthesis, and in vitro antiplasmodial activity of 4-aminoquinolines containing modified amino acid conjugates". . p. 1148 - 1162. Retrieved 2016/07/06.
• 2、 Mevers, Emily,Haeckl, F. P. Jake,Boudreau, Paul D.,Byrum, Tara,Dorrestein, Pieter C.,Valeriote, Frederick A.,Gerwick, William H.. "Lipopeptides from the tropical marine cyanobacterium symploca sp.". . p. 969 - 975. Retrieved 2014/05/20.