Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

331813

Sigma-Aldrich

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

99%

Synonym(s):

tert-Butyl (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):
C21H23NO4
CAS Number:
112741-50-1
Molecular Weight:
353.41
MDL number:
MFCD00074953
UNSPSC Code:
12352005
PubChem Substance ID:
24860000
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]20/D +86°, 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+/m1/s1

InChI key

MRUKRSQUUNYOFK-MOPGFXCFSA-N

Application

(2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylmorpholine (Williams chiral auxiliary) can be used as a reactant:
  • In the asymmetric synthesis of cylindrospermopsin and related alkaloids via an intramolecular 1,3-dipolar cycloaddition reaction.[1]
  • To synthesize boc-3-(1-methylcyclopropyl)-D-alanine, which is used as an intermediate to prepare 4-fluoroproline-based analogs as potent tripeptide thrombin inhibitors.[2]
  • In the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin by intramolecular 1,3-dipolar cycloaddition and nitroaldol reaction.[3]
  • To prepare differentially functionalized diaminoglutamic acids via radical reaction of selenide with methyl 2-acetamidoacrylate.[4]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCS5649
MKBQ9762V
MKBD0043
MKBB3468
02007KJ

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Syntheses of the cylindrospermopsin alkaloids
Looper RE, et al.
Tetrahedron, 62(18), 4549-4562 (2006)
Radical reaction of Williams? glycinate auxiliaries with α-amidoacrylates: synthesis of orthogonally functionalized (2R, 4R)-and (2R, 4S)-diaminoglutamic acids
Kabat MM
Tetrahedron Letters, 42(42), 7521-7524 (2001)
Discovery of potent, selective 4-fluoroproline-based thrombin inhibitors with improved metabolic stability
Staas DD, et al.
Bioorganic & Medicinal Chemistry, 14(20), 6900-6916 (2006)
A Concise Asymmetric Synthesis of the Marine Hepatotoxin 7-Epicylindrospermopsin
Looper RE and Williams RM
Angewandte Chemie (International ed. in English), 43(22), 2930-2933 (2004)

Questions

Reviews

No rating value

Active Filters

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