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
Empirical Formula (Hill Notation):
C24H21NO4
CAS Number:
Molecular Weight:
387.43
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

assay

98%

optical activity

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

mp

205-207 °C (lit.)

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

Related Categories

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.

Packaging

1 g in glass bottle
250 mg in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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)
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)
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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