63267-97-0

Basic information

• Product Name: (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one
• CAS NO: 63267-97-0
• Molecular Weight: 316.381
• Mol File: 63267-97-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one(63267-97-0)
• EPA Substance Registry System: (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one(63267-97-0)

Safety Data

• Hazardous Substances Data: 63267-97-0(Hazardous Substances Data)

Upstream product

• 63212-16-8 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one 

Downstream Products

• 63212-16-8 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-4,4-dimethylthietan-2-one 
• 74743-61-6 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3,4,4-trimethylthietan-2-one 
• 74743-62-7 (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3,4,4-trimethylthietan-2-one 
• 74743-63-8 (3R)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-t-butyloxycarbonylmethyl-4,4-dimethylthietan-2-one 
• 74743-64-9 (3S)-3-<(1S,5R)-3-benzyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>-3-t-butyloxycarbonylmethyl-4,4-dimethylthietan-2-one 
• 63211-99-4 [(Ξ)-3-((1S)-3-benzyl-7-oxo-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-2,2-dimethyl-4-oxo-thietan-3-yl]-acetic acid tert-butyl ester 

Relevant articles and documents

Studies Related to Penicillins. Part 19. Alkylations of (3R)-3-hept-2-en-6-yl>-4,4-dimethylthietan-2-one

The title compound (7a) unergoes epimerisation at position 3 of the thietanone ring in the presence of triethylamine; the equilibrium ratio of the starting material and its epimer (9a) is ca. 1.5 : 1.Methylation of the compounds (7a) or (9a) also occurs at position 3 of the thietanone ring, in the presence of sodium hydride-methyl iodide; a ca. 1 : 1 mixture of the (3R)-3-methylthietanone (7b) and the (3S)-3-methylthietanone (9b) is produced when tetrahydrofuran is used as the solvent whereas a ca. 2.5 : 1 mixture of the compounds (7b) and (9b) is formed when NN-dimethylformamide is employed.With potassium t-butoxide-t-butyl bromoacetate in NN-dimethylformamide, the thietanone (7a) affords a ca. 6 : 1 mixture of the (3R)-3-t-butyloxycarbonylmethylthietanone (7c) and its (3S)-isomer (9c).Only the (3R)-3-allylthietanone (7d) is formed when the thietanone (7a) is treated with potassium t-butoxide-allyl iodide in NN-dimethylformamide.Attempts to hydroxymethylate the thietanone (7a), by using potassium t-butoxide-formaldehyde, were thwarted by further reactions of the hydroxymethyl derivative (7e) or (9d), resulting in the formation of a mixture of 7-(α-mercapto-α-methylethyl)-3-phenylacetamido-1-aza-5,9-dioxabicyclodec-2-ene-4,8-dione (16a) and 11,11-dimethyl-5-phenylacetamido-3,9-dioxa-12-thia-7-azatricyclo1,7>dodecane-4,10-dione (20).