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
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.

Quality Level

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

Related Categories

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.

Packaging

1 g 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

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)
Asymmetric synthesis of (+)-negamycin
Jain RP and Williams RM
The Journal of Organic Chemistry, 67(18), 6361-6365 (2002)
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)

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