Boc-D-asparagine

Base Information

• Chemical Name: Boc-D-asparagine
• CAS No.: 75647-01-7
• Molecular Formula: C₉H₁₆N₂O₅
• Molecular Weight: 232.236
• Hs Code.: 29241990
• European Community (EC) Number: 231-405-2
• DSSTox Substance ID: DTXSID00364634
• Nikkaji Number: J2.650.105I
• Wikidata: Q72448518
• ChEMBL ID: CHEMBL1222169
• Mol file: 75647-01-7.mol

Synonyms:Boc-D-Asn-OH;Boc-D-asparagine;75647-01-7;Boc-L-Asn-OH;(2R)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid;(R)-4-AMINO-2-((TERT-BUTOXYCARBONYL)AMINO)-4-OXOBUTANOIC ACID;D-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-;N-BOC-D-ASPARAGINE;n-alpha-boc-d-asparagine;Nalpha-Boc-D-asparagine;Nalpha-(tert-Butoxycarbonyl)-D-asparagine;MFCD00065558;N2-[(tert-butoxy)carbonyl]-L-asparagine;N-|A-Boc-D-asparagine;BOC-(D)-Asn-OH;SCHEMBL1486143;CHEMBL1222169;DTXSID00364634;CHEBI:180549;AKOS016842899;AM81558;CS-W012936;FD21162;HY-W012220;(TERT-BUTOXYCARBONYL)-D-ASPARAGINE;AC-24165;AS-12727;Boc-D-Asn-OH, >=98.0% (TLC);B2964;N-ALPHA-T-BUTYLOXYCARBONYL-D-ASPARAGINE;EN300-1589954;J-300045;Q-101665;(2R)-2-{[(tert-butoxy)carbonyl]amino}-3-carbamoylpropanoic acid;(R)-4-AMINO-2-(TERT-BUTOXYCARBONYLAMINO)-4-OXOBUTANOIC ACID;(2R)-4-Amino-2-({[(2-methyl-2-propanyl)oxy]carbonyl}amino)-4-oxobutanoic acid

Chemical Property of Boc-D-asparagine

Chemical Property:

• Appearance/Colour: white fine crystalline powder
• Vapor Pressure: 1.33E-10mmHg at 25°C
• Melting Point: 165-169 °C
• Refractive Index: 7.7 ° (C=1, DMF)
• Boiling Point: 481.7 °C at 760 mmHg
• PKA: 3.79±0.10(Predicted)
• Flash Point: 245.1 °C
• PSA: 118.72000
• Density: 1.253 g/cm³
• LogP: 0.93090
• Storage Temp.: Store at 0°C
• Solubility.: soluble in Dimethylformamide
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 232.10592162
• Heavy Atom Count: 16
• Complexity: 295

Purity/Quality:

99%, ^*data from raw suppliers

Boc-D-asparagine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 24/25-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC(=O)N)C(=O)O
• Uses: Nα-Boc-D-asparagine is an N-Boc-protected form of D-Asparagine (A788990). D-Asparagine is an isomer of L-Asparagine (A790005) and is used by bacteria (such as Saccharomyces cerevisiae) as a sole nitrogen source for replication. L-Asparagine is also a competitive inhibitor of staphylococcal L-asparaginase and is used as a reagent to synthesize peptide antibiotics.

Technology Process of Boc-D-asparagine

There total 4 articles about Boc-D-asparagine 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: 84.0%

(R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) + di-tert-butyl dicarbonate (24424-99-5) → N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 20 ℃;

Reference yield: 80.0%

(R)-Asparagine (2058-58-4,28088-48-4,7006-34-0) → N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7)

Guidance literature:

With triethylamine; In 1,4-dioxane; water; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87142-8

Reference yield:

N-butyloxycarbonyl-D-asparagine p-nitrophenyl ester (104199-82-8) → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + N-t-butyloxycarbonyl-D-asparagine (7536-55-2,142847-17-4,75647-01-7)

Guidance literature:

With 1H-imidazole; rac-octan-2-ol; water; Bis-(S)-2-octyl sodium sulphosuccinate; In n-heptane; at 25 ℃; Rate constant; other combination <(S) or (+/-)> of reagents; pH = 8; enantioselectivity;

DOI:10.1039/c39860000597

upstream raw materials:

N-butyloxycarbonyl-D-asparagine p-nitrophenyl ester

(R)-Asparagine

di-tert-butyl dicarbonate

Downstream raw materials:

N-t-butyloxycarbonyl-D-asparagine, benzhydrylester

(S)-2-(tert-butoxycarbonylamino)pyrrolidine-2,5-dione

3-(N-tBoc-D-amino)succinimide

tert-butyl (2,5-dioxopyrrolidin-3-yl)carbamate

Refernces

• 1、 Vizcaino, Maria I.,Engel, Philipp,Trautman, Eric,Crawford, Jason M.. "Comparative metabolomics and structural characterizations illuminate colibactin pathway-dependent small molecules". supporting information. p. 9244 - 9247. Retrieved 2014/07/21.
• 2、 -. "Kinase inhibitor compounds". Page/Page column 44. . Retrieved 2009/04/24.