Boc-D-Aspartic acid

Base Information

• Chemical Name: Boc-D-Aspartic acid
• CAS No.: 62396-48-9
• Molecular Formula: C₉H₁₅NO₆
• Molecular Weight: 233.221
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID80427332
• Nikkaji Number: J761.227C
• Wikidata: Q72448524
• Mol file: 62396-48-9.mol

Synonyms:Boc-D-Aspartic acid;62396-48-9;Boc-D-Asp-OH;N-Boc-D-aspartic Acid;Boc-L-Asp-OH;(tert-Butoxycarbonyl)-D-aspartic acid;N-(tert-Butoxycarbonyl)-D-aspartic Acid;(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanedioic acid;D-Aspartic acid, N-[(1,1-dimethylethoxy)carbonyl]-;MFCD00798618;N-Boc-D-asparticAcid;N-t-boc-d-aspartic acid;SCHEMBL1486220;DTXSID80427332;AKOS015838058;AM81587;AC-24121;AC-24123;DS-15836;HY-42067;B2965;CS-0020433;EN300-1589600;A833758;N-[(1,1-dimethylethoxy)carbonyl]-D-aspartic acid;D-Aspartic acid,N-[(1,1-dimethylethoxy)carbonyl]-;Q-101670;(2R)-2-{[(tert-butoxy)carbonyl]amino}butanedioic acid;(2R)-2-[(TERT-BUTOXYCARBONYL)AMINO]BUTANEDIOIC ACID

Chemical Property of Boc-D-Aspartic acid

Chemical Property:

• Refractive Index: 5.3 ° (C=1, MeOH)
• Boiling Point: 377.4 °C at 760 mmHg
• PKA: 3.77±0.23(Predicted)
• Flash Point: 182.1 °C
• PSA: 112.93000
• Density: 1.302 g/cm³
• LogP: 0.82990
• Storage Temp.: Store at RT.
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 233.08993720
• Heavy Atom Count: 16
• Complexity: 293

Purity/Quality:

99%, ^*data from raw suppliers

N-Boc-D-asparticAcid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC(=O)O)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](CC(=O)O)C(=O)O
• Uses: N-Boc-D-aspartic acid is an N-Boc-protected form of D-Aspartic acid (A790020). D-Aspartic acid is the unnatural isomer of L-Aspartic acid (A790024). D-Aspartic acid naturally occurs in human ovarian follicular fluid, and is thought to be linked to oocyte quality. It is also found in the white matter of human brains, more specifically in myelin proteins.

Technology Process of Boc-D-Aspartic acid

There total 2 articles about Boc-D-Aspartic acid 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: 63.0%

(2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + di-tert-butyl dicarbonate (24424-99-5) → Nα-(tert-butyloxycarbonyl)-D-aspartic acid (13726-67-5,62396-48-9,120341-32-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; at 20 ℃; Cooling with ice;

DOI:10.1021/jo102592f

Reference yield:

BOC-asn-PNP → 4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) + Nα-(tert-butyloxycarbonyl)-D-aspartic acid (13726-67-5,62396-48-9,120341-32-4)

Guidance literature:

With (S)-2-Octanol; borate buffer; water; Bis-2-octyl sodium sulphosuccinate; 1H-imidazole; In n-heptane; at 25 ℃; Rate constant; k^D; pH= 8.0; other racemic or chiral surfactant and cosurfactants and other proportions of water and surfactant;

DOI:10.1016/S0040-4020(01)89932-4

Reference yield: 90.0%

benzyl bromide (100-39-0) + N-t-Boc-L-aspartic acid (13726-67-5,62396-48-9,120341-32-4) → 2-tert-Butoxycarbonylamino-succinic acid dibenzyl ester (80974-42-1)

Guidance literature:

With potassium hydroxide; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80104-0

upstream raw materials:

(2R)-aspartic acid

di-tert-butyl dicarbonate

Downstream raw materials:

2-tert-Butoxycarbonylamino-succinic acid dibenzyl ester

(R)-2-tert-Butoxycarbonylamino-succinic acid 1-(9H-fluoren-9-ylmethyl) ester

C₃₀H₂₉FN₄O₅S

C₃₀H₂₉FN₄O₅S

Refernces

• 1、 Dacquarica, Ilaria,Cerreto, Antonella,Delle Monache, Giuliano,Subrizi, Fabiana,Boffi, Alberto,Tafi, Andrea,Forli, Stefano,Botta, Bruno. "N-linked peptidoresorc[4]arene-based receptors as noncompetitive inhibitors for α-chymotrypsin". experimental part. p. 4396 - 4407. Retrieved 2011/07/08.