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440655

Sigma-Aldrich

Boc-Asp(OBzl)-OH

98%

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Synonym(s):
N-(tert-Butoxycarbonyl)-L-aspartic acid 4-benzyl ester, Boc-L-aspartic acid 4-benzyl ester
Linear Formula:
C6H5CH2OCOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
Molecular Weight:
323.34
Beilstein:
2064127
EC Number:
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

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.

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)

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De Lombaert, S. et al.
Tetrahedron Letters, 35, 7513-7513 (1994)
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
Vitamin K1 dependent carboxylase: beta-carboxylation of t-butyloxycarbonylaspartic acid alpha-benzyl ester.
S E Hamilton et al.
Biochemical and biophysical research communications, 107(1), 246-249 (1982-07-16)
Bland, J.M.
Synthetic Communications, 25, 467-467 (1995)

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