Boc-d-tert-leucine

Base Information

• Chemical Name: Boc-d-tert-leucine
• CAS No.: 124655-17-0
• Molecular Formula: C11H21NO4
• Molecular Weight: 231.292
• Hs Code.: 2924190090
• European Community (EC) Number: 676-419-3
• DSSTox Substance ID: DTXSID40426487
• Wikidata: Q72450768
• Mol file: 124655-17-0.mol

Synonyms:124655-17-0;boc-d-tert-leucine;N-Boc-D-tert-leucine;boc-d-tle-oh;(r)-n-(tert-butoxycarbonyl)-tert-leucine;(R)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid;D-Valine, N-[(1,1-dimethylethoxy)carbonyl]-3-methyl-;BOC-D-ALPHA-T-BUTYLGLYCINE;(2R)-3,3-dimethyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid;(R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3,3-dimethylbutanoic acid;MFCD00065575;N-Boc-D-tert-butylglycine;SCHEMBL83699;DTXSID40426487;LRFZIPCTFBPFLX-ZETCQYMHSA-N;HY-I0377;AKOS016842367;CS-W019690;GS-6444;Boc-D-alpha-t-butylglycine, AldrichCPR;N-(tert-Butoxycarbonyl)-D-tert-leucine;AC-24091;AM808134;N-(tert-butoxycarbonyl)-3-methyl-D-valine;B3995;(R)-N-Boc-2-amino-3,3-dimethylbutyric acid;N-ALPHA-T-BUTYLOXYCARBONYL-D-T-LEUCINE;(R)-2-(Boc-amino)-3,3-dimethylbutyric Acid;EN300-127899;A805271;Q-102760;N-{[(1,1-dimethylethyl)oxy]carbonyl}-3-methyl-D-valine;(R)-2-(tert-Butoxycarbonylamino)-3,3-dimethylbutyric Acid;(R)-2-TERT-BUTOXYCARBONYLAMINO-3,3-DIMETHYL-BUTYRIC ACID;(2R)-2-(tert-butoxycarbonylamino)-3,3-dimethyl-butanoic acid

Chemical Property of Boc-d-tert-leucine

Chemical Property:

• Vapor Pressure: 7.8E-06mmHg at 25°C
• Melting Point: 118-121 °C
• Refractive Index: 1.462
• Boiling Point: 350 °C at 760 mmHg
• PKA: 4.03±0.10(Predicted)
• Flash Point: 165.5 °C
• PSA: 75.63000
• Density: 1.063 g/cm³
• LogP: 2.40130
• Storage Temp.: Store at 0-5°C
• Solubility.: slightly sol. in Methanol
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 231.14705815
• Heavy Atom Count: 16
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-D-tert-leucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Boc-d-tert-leucine

There total 16 articles about Boc-d-tert-leucine 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: 97.0%

→ (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (124655-17-0)

Guidance literature:

Reference yield: 83.0%

D-tert-leucine (26782-71-8) + di-tert-butyl dicarbonate (24424-99-5) → (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (124655-17-0)

Guidance literature:

With sodium hydroxide; In methanol; water; at 0 - 20 ℃;

Reference yield: 52.0%

C14H21F6NO4 → N-tert-butyloxycarbonyl-L-tert-leucine (62965-35-9) + (R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (124655-17-0)

Guidance literature:

With C₂₈H₃₀N₃O₂⁽¹⁺⁾*Br^(1-); sodium hydroxide; In chloroform; at 0 ℃; for 24h;

DOI:10.1021/acscatal.8b00693

upstream raw materials:

(R)-2-N-<(1,1-dimethylethoxy)carbonyl>amino-3,3-dimethylbutanol

N-Boc-D-tert-leucine methyl ester

di-tert-butyl dicarbonate

(4R, 5S)-4-tert-butyl-5-(1,2-bis(isopropoxycarbonyl)hydrazino)-2-oxazolidinone

Downstream raw materials:

N-boc-D-tert-leucine(salicylaldehyde) ester

tert-butyl (R)-1-((S)-2-(3-chlorobenzylcarbamoyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

(S)-benzyl 1-((R)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoyl)pyrrolidine-2-carboxylate

(R)-benzyl 2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoate

Refernces

• 1、 Cai, Zedong,Lan, Ting,Ma, Pengfei,Zhang, Jingfang,Yang, Qingqing,He, Wei. "A new type of L-Tertiary leucine-derived ligand: Synthesis and application in Cu(II)-catalyzed asymmetric Henry reactions". . . Retrieved 2019/08/08.
• 2、 Alicea-Matías, Eyleen,Soderquist, John A.. "Asymmetric Propargylboration of Aldimines and Ketimines with the Borabicyclo[3.3.2]decanes: Novel Entries to Allenyl Carbinamines, Amino Acids, and Their α-Methyl Counterparts". supporting information. p. 336 - 339. Retrieved 2017/04/21.