254442-06-3

Basic information

• Product Name: (4R,5S)-3-(4-Chloro-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one
• Synonyms: (4R,5S)-3-(4-Chloro-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one
• CAS NO: 254442-06-3
• Molecular Weight: 281.739
• Mol File: 254442-06-3.mol

Chemical Properties

• CAS DataBase Reference: (4R,5S)-3-(4-Chloro-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-3-(4-Chloro-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one(254442-06-3)
• EPA Substance Registry System: (4R,5S)-3-(4-Chloro-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one(254442-06-3)

Safety Data

• Hazardous Substances Data: 254442-06-3(Hazardous Substances Data)

Upstream product

• 77943-39-6 4-methyl-5-phenyloxazolidin-2-one 
• 4635-59-0 4-Chlorobutanoyl chloride 

Downstream Products

• 137664-51-8 (4R,5S)-3-((R)-4-Azido-2-methyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 254441-78-6 (4R,5S)-3-(4-Azido-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one 

Relevant articles and documents

Calyculin synthetic studies. 2. Stereocontrolled assembly of the C(9)-C(13) dithiane and C(26)-C(37) oxazole intermediates

The C(9)-C(13) dithiane (+)-2 and C(26)-C(37) γ-amino acid/oxazole (+)-5, key building blocks for calyculin total synthesis, have been elaborated in homochiral form. Noteworthy features of the schemes include stereocontrolled generation of the C(36) steeo

Total synthesis of (+)-calyculin A and (-)-calyculin B: Cyanotetraene construction, asymmetric synthesis of the C(26-37) oxazole, fragment assembly, and final elaboration

A convergent total synthesis leading to (+)-calyculin A and (-)-calyculin B (1 and 2), antipodes of the potent, highly selective and remarkably cell-permeable phosphatase inhibitors calyculins A and B, has been achieved. In the preceding paper we outlined the asymmetric synthesis of the C(9-25) spiroketal dipropionate subunit (+)-BC; herein we describe construction of the C(1-8) cyanotetraene, an asymmetric synthesis of the C(26-37) oxazole, fragment assembly and final elaboration to (+)-1 and (-)-2. Highlights of the synthesis include: application of a one-pot three-component Suzuki reaction for the construction of phosphonate A, a bifunctional triene precursor of the light sensitive C(1-8) cyanotetraene subunit, an asymmetric synthesis of the C(26-32) oxazole (-)-D, exploiting the Silks-Odom 77Se NMR protocol to assess enantiomeric purity, construction of the C(33-37) subtarget (-)-E in a highly stereocontrolled fashion via an acyliminium ion, and a concise, highly efficient sequence for fragment assembly and elaboration to (+)-calyculin A and (-)-calyculin B. The synthesis of (-)-2 also confirms the structure of calyculin B, previously based only on spectral comparison with calyculin A.