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Merck
CN

331813

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

99%

Synonym(s):

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

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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

Key Documents

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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.
  • 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.

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
MKCS5649
MKBQ9762V
MKBD0043
MKBB3468
02007KJ

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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)
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)
Syntheses of the cylindrospermopsin alkaloids
Looper RE, et al.
Tetrahedron, 62(18), 4549-4562 (2006)

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