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Merck
CN

440655

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
EC Number:
231-406-8
UNSPSC Code:
12352200
PubChem Substance ID:
24867616
Beilstein/REAXYS Number:
2064127
MDL number:
MFCD00065564

Key Documents

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InChI key

SOHLZANWVLCPHK-LBPRGKRZSA-N

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

SMILES string

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

assay

98%

optical activity

[α]20/D −19.5°, c = 2 in DMF

mp

98-102 °C (lit.)

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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

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

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

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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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