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331848

Sigma-Aldrich

(2R,3S)-(−)-N-Boc-6-oxo-2,3-diphenylmorpholine

98%

Synonym(s):

tert-Butyl (2R,3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

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About This Item

Empirical Formula (Hill Notation):
C21H23NO4
CAS Number:
112741-49-8
Molecular Weight:
353.41
MDL number:
MFCD00074955
UNSPSC Code:
12352005
PubChem Substance ID:
24860002
NACRES:
NA.22

Assay

98%

optical activity

[α]25/D −87°, c = 5.5 in methylene chloride

optical purity

ee: 99% (HPLC)

mp

206 °C (dec.) (lit.)

functional group

ester
phenyl

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)N1CC(=O)O[C@@H]([C@@H]1c2ccccc2)c3ccccc3

InChI

1S/C21H23NO4/c1-21(2,3)26-20(24)22-14-17(23)25-19(16-12-8-5-9-13-16)18(22)15-10-6-4-7-11-15/h4-13,18-19H,14H2,1-3H3/t18-,19+/m0/s1

InChI key

MRUKRSQUUNYOFK-RBUKOAKNSA-N

Application

(2R,3S)-(-)-N-Boc-6-oxo-2,3-diphenylmorpholine (Williams′ morpholinone) can be used as a reactant to prepare:
  • Indole substituted tryptophan derivatives by alkylation with quaternary gramine in the presence of a base.
  • Tyrosine derivatives, which can be utilized as building blocks for the total synthesis of ecteinascidin and safracin family of alkaloids.

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
MKBJ2300V
MKBC1009
MKBB1162
04501HD
08729MC

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Synthetic studies on ecteinascidin 743: asymmetric synthesis of the versatile amino acid component
Jin, Wei and Williams, Robert M
Tetrahedron Letters, 44(25), 4635-4639 (2003)
Synthesis of tryptophans by alkylation of chiral glycine enolate equivalents with quaternary gramines
Reinfelds, M, et al.
Tetrahedron Letters, 56(43), 5882-5885 (2015)

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