(2S,3R)-tert-Butyl 6-oxo-2,3-diphenylmorpholine-4-carboxylate , 95% , 112741-50-1

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

Update time: 2022-07-08

Melting point:	206 °C (dec.)(lit.)
alpha	86 º (c=5.5 in methylene chloride)
Boiling point:	509.6±50.0 °C(Predicted)
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)

(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.