Skip to Content
MilliporeSigma
All Photos(1)

Documents

331856

Sigma-Aldrich

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

99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C24H21NO4
CAS Number:
105228-46-4
Molecular Weight:
387.43
MDL number:
MFCD00074956
UNSPSC Code:
12352005
PubChem Substance ID:
24860003
NACRES:
NA.22

assay

99%

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+/m1/s1

InChI key

HECRUWTZAMPQOS-PKTZIBPZSA-N

Application

(2S,3R)-(+)-N-Z-6-oxo-2,3-diphenylmorpholine can be used as a starting material for the synthesis of:
  • α-Amino-β-silyloxy-ester, a key intermediate for the preparation of antimalarial drug quinine and its analogs.
  • R, R-Formylglycine dimethylacetal, a key intermediate for the preparation of tuberculostatic compound capreomycin IB.
  • 2R,5R,6S-2-(Methoxycarbonylmethyl)-5,6-diphenylmorpholine hydrochloride, a key intermediate for the preparation of an antibiotic (+)-negamycin.

pictograms

Exclamation mark
GHS07

signalword

Warning

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Asymmetric synthesis of (+)-negamycin
Jain RP and Williams RM
The Journal of Organic Chemistry, 67(18), 6361-6365 (2002)
Asymmetric synthesis of (2S, 3R)-capreomycidine and the total synthesis of capreomycin IB
DeMong DE and Williams RM
Journal of the American Chemical Society, 125(28), 8561-8565 (2003)
Synthetic studies on quinine: quinuclidine construction via a Ketone Enolate regio-and diastereoselective Pd-mediated allylic alkylation
Johns DM, et al.
Organic Letters, 8(18), 4051-4054 (2006)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service