Boc-asn-obzl

Base Information

• Chemical Name: Boc-asn-obzl
• CAS No.: 13512-57-7
• Molecular Formula: C16H22N2O5
• Molecular Weight: 322.361
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50560088
• Nikkaji Number: J81.632I
• Wikidata: Q72470097
• Mol file: 13512-57-7.mol

Synonyms:BOC-ASN-OBZL;13512-57-7;(S)-Benzyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate;benzyl (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate;(S)-benzyl 4-amino-2-(tert-butoxycarbonylamino)-4-oxobutanoate;MFCD00190784;L-Asparagine, N2-[(1,1-dimethylethoxy)carbonyl]-, phenylmethyl ester;Benzyl N~2~-(tert-butoxycarbonyl)-L-asparaginate;benzyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-carbamoylpropanoate;SCHEMBL7297130;DTXSID50560088;VNFPRPGXGYMAKL-LBPRGKRZSA-N;AKOS016843989;DS-4307;FD21209;Benzyl (tert-butoxycarbonyl)-L-asparaginate;CS-0154518;tert.butyloxycarbonyl-l-asparagine benzyl ester;L-Asparagine,n2-[(1,1-dimethylethoxy)carbonyl]-,phenylmethyl ester;(S)-BenZyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate (Boc-L-Asn-OBZl)

Chemical Property of Boc-asn-obzl

Chemical Property:

• Vapor Pressure: 1.14E-11mmHg at 25°C
• Melting Point: 124-126℃
• Refractive Index: 1.527
• Boiling Point: 538.624 °C at 760 mmHg
• PKA: 10.89±0.46(Predicted)
• Flash Point: 279.55 °C
• PSA: 107.72000
• Density: 1.188 g/cm³
• LogP: 2.58970
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 322.15287181
• Heavy Atom Count: 23
• Complexity: 425

Purity/Quality:

98%min ^*data from raw suppliers

Boc-?Asn-?OBzl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)OCC1=CC=CC=C1
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC(=O)N)C(=O)OCC1=CC=CC=C1
• Uses: Boc-?Asn-?OBzl is a useful reactant that is used to isolate a new metabolite from a pks+ E. coli mutant missing an essential biosynthetic enzyme.

Technology Process of Boc-asn-obzl

There total 9 articles about Boc-asn-obzl 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: 88.0%

N-tert-butyloxycarbonylasparagine (7536-55-2) + benzyl bromide (100-39-0) → N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester (13512-57-7)

Guidance literature:

N-tert-butyloxycarbonylasparagine; With caesium carbonate; In methanol; water; at 25 ℃; for 4h;

benzyl bromide; In N,N-dimethyl-formamide; at 25 ℃; for 14h;

DOI:10.1016/S0968-0896(98)00090-X

Reference yield: 87.0%

N-tert-butyloxycarbonylasparagine (7536-55-2) + (4-hydroxyphenyl)(methyl)(benzyl)sulfonium chloride → N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester (13512-57-7)

Guidance literature:

With potassium carbonate; In dichloromethane; N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1246/bcsj.69.1099

Reference yield: 51.0%

benzyl bromide (100-39-0) → N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine benzyl ester (13512-57-7)

Guidance literature:

N-tert-butyloxycarbonylasparagine; With caesium carbonate; In methanol;

benzyl bromide; In DMF (N,N-dimethyl-formamide);

upstream raw materials:

N-tert-butyloxycarbonylasparagine

benzyl bromide

di-tert-butyl dicarbonate

Cesium salt of BOC-Asparagine

Downstream raw materials:

L-asparagine benzyl ester trifluoroacetate

C₂₅H₄₀N₂O₄

O-benzyl-L-asparagine

(1-{3-[5-(3,4-dimethoxy-phenylcarbamoyl)-1H-indol-2-yl]-propylcarbamoyl}-2-thiazol-2-yl-ethyl)-(S)-carbamic acid tert-butyl ester

Refernces

• 1、 Brotherton, Carolyn A.,Wilson, Matthew,Byrd, Gary,Balskus, Emily P.. "Isolation of a metabolite from the pks island provides insights into colibactin biosynthesis and activity". supporting information. p. 1545 - 1548. Retrieved 2015/03/30.
• 2、 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.