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331813 Sigma-Aldrich

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

99%

Synonym: tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

  • CAS Number 112741-50-1

  • Empirical Formula (Hill Notation) C21H23NO4

  • Molecular Weight 353.41

  •  MDL number MFCD00074953

  •  PubChem Substance ID 24860000

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Heterocyclic Building Blocks, Morpholines More...
Quality Level   100
assay   99%
optical activity   [α]20/D +86°, c = 5.5 in methylene chloride
optical purity   ee: 99% (HPLC)
mp   206 °C (dec.) (lit.)
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

Description

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.
• 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.
•  In the total synthesis of potent hepatotoxic alkaloid 7-epicylindrospermopsin by intramolecular 1,3-dipolar cycloaddition and nitroaldol reaction.
• To prepare differentially functionalized diaminoglutamic acids via radical reaction of selenide with methyl 2-acetamidoacrylate.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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