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Merck
CN

331856

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

99%

Synonym(s):

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

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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

Key Documents

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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

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
07507PD
13616ED
07620DF
05522TF
03202HF

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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)
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)

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