106930-51-2

Basic information

• Product Name: BOC-D-LEUCINOL
• Synonyms: (R)-N-(T-BUTOXYCARBONYL)-LEUCINOL;R(+)-2-(BOC-AMINO)-4-METHYL-1-PENTANOL;N-T-BUTOXYCARBONYL-D-LEUCINOL;N-T-BOC-D-LEUCINOL;N-ALPHA-T-BOC-D-LEUCINOL;N-BOC-D-LEUCINOL;BOC-(R)-2-AMINO-4-METHYL-1-PENTANOL;BOC-D-LEUCINOL
• CAS NO: 106930-51-2
• Molecular Formula: C₁₁H₂₃NO₃
• Molecular Weight: 217.31
• Product Categories: Amino Acids
• Mol File: 106930-51-2.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 213 °C(lit.)
• Flash Point: >230 °F
• Appearance: Colorless/Liquid
• Density: 0.983 g/mL at 25 °C(lit.)
• Vapor Pressure: 2.8E-05mmHg at 25°C
• Refractive Index: n20/D 1.449(lit.)
• Storage Temp.: Store at 0°C
• PKA: 12.11±0.46(Predicted)
• CAS DataBase Reference: BOC-D-LEUCINOL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-LEUCINOL(106930-51-2)
• EPA Substance Registry System: BOC-D-LEUCINOL(106930-51-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 106930-51-2(Hazardous Substances Data)

Usage

Chemical Properties

Solid

InChI:InChI=1/C11H23NO3/c1-8(2)6-9(7-13)12-10(14)15-11(3,4)5/h8-9,13H,6-7H2,1-5H3,(H,12,14)/t9-/m1/s1

Upstream product

• 7533-40-6 2-amino-4-methyl-1-pentanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 328-38-1 (R)-leucine 
• 1234196-13-4 2-(tert-butoxycarbonylamino)-4-methylpentyl acetate 
• 219819-68-8 tert-butyl (R)-2-(((tert-butyldimethylsilyl)oxy)-methyl)aziridine-1-carboxylate 
• 152491-85-5 (R)-[1-(tert-butyl-dimethyl-silanyloxymethyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 
• 126645-26-9 (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-((tert-butyldimethylsilyl)oxy)propanoate 
• 2766-43-0 N-tert-butyloxycarbonyl-L-serine methyl ester 
• 133467-01-3 methyl (2R)-2-(tert-butoxycarbonylamino)-4-methylpentanoate 
• 16937-99-8 N-Boc-D-Leu 

Downstream Products

• 321328-70-5 ((R)-1-aminomethyl-3-methyl-butyl)-carbamic acid tert-butyl ester 
• 230637-48-6 tert-butyl [(3R)-1-hydroxy-5-methylhexan-3-yl]carbamate 
• 832711-50-9 [3-methyl-1-[[[(4-methylphenyl)sulfonyl]oxy]methyl]butyl]-1,1-dimethylethyl carbamic ester 
• 732282-63-2 (R)-3-(N-tert-butoxycarbonyl-2-amino-4-methylpentyl)-1-(2,6-difluorobenzyl)-5-(2-fluoro-3-methoxyphenyl)-6-methyluracil 
• 352290-77-8 3-(2-amino-4-methyl-pentyl)-1-(2,6-difluoro-benzyl)-5-(2-fluoro-3-methoxy-phenyl)-6-methyl-1H-pyrimidine-2,4-dione 
• 732282-62-1 (R)-5-bromo-3-(N-tert-butoxycarbonyl-2-amino-4-methylpentyl)-1-(2,6-difluorobenzyl)-6-methyluracil 
• 16937-99-8 N-Boc-D-Leu 
• 116662-96-5 (2R)-2-(1,1-dimethylethoxycarbonylamino)-4-methylpentanal 

Relevant articles and documents

A Synthesis of Statine Utilizing an Oxidative Route to Chiral α-Amino Aldehydes

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Urea based foldamers

N,N′-linked oligoureas are a class of enantiopure, sequence-defined peptidomimetic oligomers without amino acids that form well-defined and predictable helical structures akin to the peptide α-helix. Oligourea-based foldamers combine a number of features—such as synthetic accessibility, sequence modularity, and folding fidelity—that bode well for their use in a range of applications from medicinal chemistry to catalysis. Moreover, it was recently recognized that this synthetic helical backbone can be combined with regular peptides to generate helically folded peptide-oligourea hybrids that display additional features in terms of helix mimicry and protein-surface recognition properties. Here we provide detailed protocols for the preparation of requested monomers and for the synthesis and purification of homo-oligoureas and peptide-oligourea hybrids.

Pd-catalyzed reductive cleavage of N-N bond in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates with PMHS: Application to a formal enantioselective synthesis of (R)-sitagliptin

An environmentally benign approach involving Pd-catalyzed reductive N-N bond cleavage in dibenzyl-1-alkylhydrazine-1,2-dicarboxylates leading to the synthesis of N-(tert-butoxy)carbamates under very mild conditions has been described. PMHS serves as an inexpensive source of hydride in MeOH/deionized H2O medium. This protocol has been successfully applied in the formal synthesis of (R)-sitagliptin, an anti-diabetic drug.