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440655

Sigma-Aldrich

Boc-Asp(OBzl)-OH

98%

Synonym(s):

N-(tert-Butoxycarbonyl)-L-aspartic acid 4-benzyl ester, Boc-L-aspartic acid 4-benzyl ester

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About This Item

Linear Formula:
C6H5CH2OCOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
7536-58-5
Molecular Weight:
323.34
Beilstein:
2064127
EC Number:
231-406-8
MDL number:
MFCD00065564
UNSPSC Code:
12352200
PubChem Substance ID:
24867616

Assay

98%

optical activity

[α]20/D −19.5°, c = 2 in DMF

mp

98-102 °C (lit.)

SMILES string

[H][C@@](CC(=O)OCc1ccccc1)(NC(=O)OC(C)(C)C)C(O)=O

InChI

1S/C16H21NO6/c1-16(2,3)23-15(21)17-12(14(19)20)9-13(18)22-10-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,19,20)/t12-/m0/s1

InChI key

SOHLZANWVLCPHK-LBPRGKRZSA-N

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Application

Starting material for the enantiospecific synthesis of (R)-(+)-Boc-iturinic acid (n-C14), the L-aspartic series of thrombin inhibitors, and diketopiperazine tetrapeptides. Used in the preparation of a novel tricyclic dipeptide mimetic based on a [6H]-azepino indoline nucleus.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
01028BJ
02519JH
13511EH
16623DB
09127BB

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Bergeron, R.J. et al.
Journal of the American Chemical Society, 116, 8479-8479 (1994)
K Hilpert et al.
Journal of medicinal chemistry, 37(23), 3889-3901 (1994-11-11)
Thrombin, a serine protease, plays a central role in the initiation and propagation of thrombotic events. An extensive search for new thrombin inhibitors was performed, using an unconventional approach. Screening of small basic molecules for binding in the recognition pocket
De Lombaert, S. et al.
Tetrahedron Letters, 35, 7513-7513 (1994)
Bland, J.M.
Synthetic Communications, 25, 467-467 (1995)
Nicole Niklas et al.
Dalton transactions (Cambridge, England : 2003), (1)(1), 154-162 (2006-12-13)
The amino acid derivative Boc-Asp-OBzl (Boc=N-butyloxycarbonyl; Asp=aspartic acid; Bzl=benzyl) was functionalized by coupling its carboxylate side chain to dipicolylamine. This yielded the tridentate nitrogen donor ligand Boc-Asp(Dpa)-OBzl (-OBzl). The compound -OBzl contains three different carbonyl groups: a tertiary amide linkage
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