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331872

Sigma-Aldrich

(2R,3S)-(−)-N-Z-6-oxo-2,3-diphenylmorpholine

98%

Synonym(s):

Benzyl (2R,3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C24H21NO4
CAS Number:
100516-54-9
Molecular Weight:
387.43
MDL number:
MFCD00074958
UNSPSC Code:
12352005
PubChem Substance ID:
24860004
NACRES:
NA.22

Assay

98%

form

solid

optical activity

[α]25/D −66°, c = 5.5 in methylene chloride

mp

205-207 °C (lit.)

functional group

ester
phenyl

storage temp.

2-8°C

SMILES string

O=C1CN([C@H]([C@H](O1)c2ccccc2)c3ccccc3)C(=O)OCc4ccccc4

InChI

1S/C24H21NO4/c26-21-16-25(24(27)28-17-18-10-4-1-5-11-18)22(19-12-6-2-7-13-19)23(29-21)20-14-8-3-9-15-20/h1-15,22-23H,16-17H2/t22-,23+/m0/s1

InChI key

HECRUWTZAMPQOS-XZOQPEGZSA-N

Application

(2R,3S)-(−)-N-Z-6-oxo-2,3-diphenylmorpholine is a Williams chiral auxiliary, which can be used:
  • As a template in the preparation of Fmoc-L-cyclopentylglycine, which acts as an angiotensin II antagonist.
  • In the synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH, a building block for the synthesis of peptidomimetics.
  • To introduce chirality in the modified amino acid named N-Fmoc 4-(2′-(di-tert-butylmalonyl))-l-phenylalanine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - 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
MKBD3072V
MKBD3072
13518KR
10407LO
10107LC

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Stereoselective preparation of L-4-(2′-malonyl) phenylalanine suitably protected for Fmoc-based synthesis of potent signal transduction inhibitory ligands
Gao Y and Burke Jr TR
Synlett, 2000(01), 134-136 (2000)
An efficient asymmetric synthesis of Fmoc-L-cyclopentylglycine via diastereoselective alkylation of glycine enolate equivalent
Singh S and Pennington MW
Tetrahedron Letters, 44(13), 2683-2685 (2003)
Enantioselective synthesis of (L)-Fmoc-alpha-Me-Lys (Boc)-OH via diastereoselective alkylation of oxazinone as a chiral auxiliary
Chauhan SS
Tetrahedron Letters, 50(49), 6913-6915 (2009)

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