124655-17-0

Basic information

• Product Name: BOC-D-ALPHA-T-BUTYLGLYCINE
• Synonyms: BOC-TBU-D-GLY-OH;BOC-D-(TBU)GLY-OH;BOC-D-T-BUTYLGLYCINE;BOC-D-TERT-LEUCINE;BOC-D-TLE-OH;BOC-D-ALPHA-T-BUTYLGLYCINE;BOC-D-ALPHA-T-BUTYL-GLY-OH;N-ALPHA-T-BOC-D-ALPHA-T-BUTYLGLYCINE
• CAS NO: 124655-17-0
• Molecular Formula: C₁₁H₂₁NO₄
• Molecular Weight: 231.29
• Product Categories: CHIRAL COMPOUNDS;Amino Acids;Amino Acids & Deriv.;CHIRAL CHEMICALS;Peptide
• Mol File: 124655-17-0.mol
• Article Data: 14

Chemical Properties

• Melting Point: 118-121°C
• Boiling Point: 350 °C at 760 mmHg
• Flash Point: 165.5 °C
• Appearance: /Solid
• Density: 1.063 g/cm³
• Vapor Pressure: 7.8E-06mmHg at 25°C
• Refractive Index: 1.462
• Storage Temp.: Store at 0-5°C
• Solubility: slightly sol. in Methanol
• PKA: 4.03±0.10(Predicted)
• CAS DataBase Reference: BOC-D-ALPHA-T-BUTYLGLYCINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-D-ALPHA-T-BUTYLGLYCINE(124655-17-0)
• EPA Substance Registry System: BOC-D-ALPHA-T-BUTYLGLYCINE(124655-17-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 124655-17-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-Boc-D-tert-leucine is a protected form of D-tert-leucine, and is used in the synthesis of primary amino acid derivatives (e.g. Desacetyl Desmethyl Lacosamide [D288325]) that possess anticonvulsant and neuropathic pain protection properties.

InChI:InChI=1/C11H21NO4/c1-10(2,3)7(8(13)14)12-9(15)16-11(4,5)6/h7H,1-6H3,(H,12,15)(H,13,14)/t7-/m0/s1

Upstream product

• 630-19-3 pivalaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 330455-53-3 (E)-N-(2,2-dimethylpropylidene)diphenylmethanamine 
• 26782-71-8 D-tert-leucine 
• 142618-89-1 (4R, 5S)-4-tert-butyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone 
• 153960-35-1 N-Boc-D-tert-leucine methyl ester 
• 142618-92-6 (R)-2-N-<(1,1-dimethylethoxy)carbonyl>amino-3,3-dimethylbutanol 

Downstream Products

• 1044499-22-0 N-boc-D-tert-leucine(salicylaldehyde) ester 
• 1334673-85-6 2-cyclopropyl-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-hydroxy-4-phenylpiperidine-1-carbonyl)-2,2-dimethylpropyl]amide 
• 1334674-10-0 2-cyclohexyloxy-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyanopiperidine-1-carbonyl)-2,2-dimethylpropyl]amide 
• 1334675-19-2 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-hydroxy-4-phenylpiperidine-1-carbonyl)-2,2-dimethylpropyl]amide 
• 1334675-85-2 2-cyclohexyloxy-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-1-(4-cyanopiperidine-1-carbonyl)-2,2-dimethylpropyl]amide 
• 442568-35-6 (R)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoate 
• 26782-71-8 D-tert-leucine 
• 242483-79-0 tert-butyl (R)-(3,3-dimethyl-1-(6-nitro-1H-benzo[d][1,2,3]triazol-1-yl)-1-thioxobutan-2-yl)carbamate 

Relevant articles and documents

Asymmetric Dearomative Cascade Multiple Functionalizations of Activated N-Alkylpyridinium and N-Alkylquinolinium Salts

An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to give bridged frameworks via repetitive dearomatization and aromatization activation.

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.

COMPOUNDS AND RELATED METHODS OF USE

Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.