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ChemicalBook >  Product Catalog >  Organic Chemistry >  Carboxylic acids and derivatives >  tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate

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

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

Product Name:
tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate
Synonyms:
  • (2S,3R)-6-Oxo-2,3-diphenyl-morpholine-4-carboxylic acid tert-butyl ester
  • (5S,6R)-(+)-4-Boc-5,6-diphenyl-2-Morpholinone, 99%
  • (2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylMorpholine
  • (5R,6S)-N-Boc-5,6-diphenyl-2-morpholinone
  • tert-butyl (2S,3R)-6-oxo-2,3-diphenylMorpholine-4-carboxylate
  • (2S,3R)-(+)-N-Boc-6-oxo-2,3-diphenylMorpholine
  • (2S, 3R) - (+) - N- t-butoxycarbonyl-6-oxo-2,3-diphenyl-Morpholine
  • (2S,3R)-tert-Butyl
CAS:
112741-50-1
MF:
C21H23NO4
MW:
353.41
EINECS:
627-150-5
Product Categories:
  • Chiral Building Blocks
  • Heterocyclic Building Blocks
  • Morpholines
  • API intermediates
Mol File:
112741-50-1.mol
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tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Chemical Properties

Melting point:
206 °C (dec.)(lit.)
Boiling point:
509.6±50.0 °C(Predicted)
alpha 
86 º (c=5.5 in methylene chloride)
Density 
1.175±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
soluble in THF, CH2Cl2
form 
solid
pka
-3.28±0.60(Predicted)
Appearance
White to off-white Solid
optical activity
[α]20/D +86°, c = 5.5 in methylene chloride
InChI
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
InChIKey
MRUKRSQUUNYOFK-MOPGFXCFSA-N
SMILES
N1(C(OC(C)(C)C)=O)CC(=O)O[C@@H](C2=CC=CC=C2)[C@H]1C1=CC=CC=C1
CAS DataBase Reference
112741-50-1(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3

MSDS

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tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate Usage And Synthesis

Uses

(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.

Synthesis

Tert-Butyl (2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate could be synthesize via a three-step procedure from erythro-2-amino-1,2-diphenylethanol

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