331872

(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: 100516-54-9
• Molecular Weight: 387.43
• MDL number: MFCD00074958
• UNSPSC Code: 12352005
• PubChem Substance ID: 24860004
• NACRES: NA.22

Properties

• 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

Description

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.[1]
• In the synthesis of (L)-Fmoc-α-Me-Lys(Boc)-OH, a building block for the synthesis of peptidomimetics.[2]
• To introduce chirality in the modified amino acid named N-Fmoc 4-(2′-(di-tert-butylmalonyl))-l-phenylalanine.[3]

Safety Information

• Pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves