404344-61-2

Basic information

• Product Name: (2S,3S)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane
• CAS NO: 404344-61-2
• Molecular Weight: 720.797
• Mol File: 404344-61-2.mol

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane(404344-61-2)
• EPA Substance Registry System: (2S,3S)-3-(1',2',3',4'-tetra-O-acetyl-D-arabino-tetritol-1'-yl)-2-[4-benzyl-2-(4-methoxyphenyl)-1,3-dioxo-2,4-diazapentyl]-2-phenylthiirane(404344-61-2)

Safety Data

• Hazardous Substances Data: 404344-61-2(Hazardous Substances Data)

Upstream product

• 3891-58-5 2,3,4,5-tetra-O-acetyl-D-arabinose 
• 173094-32-1 3-(4-methoxyphenyl)-2-(N-methylbenzylamino)-5-phenyl-1,3-thiazolium-4-olate 

Relevant articles and documents

1,3-Dipolar cycloaddition of 2-dialkylaminothioisomuenchnones with aliphatic aldehydes: Synthesis of β-lactams and thiiranes, structure elucidation, and rationale for chemoselective fragmentation of cycloadducts

A series of highly funtionalized β-lactams and thiiranes can be generated on treatment of 1,3-thiazolium-4-olates (thioisomuenchnones) with aliphatic aldehydes. Although in some cases a variety of products have been obtained, the present paper now provides a mechanistic rationale to explain the product distribution based on stereoelectronic effects. Thus, ring fragmentation of the initial [3+2] cycloadduct is essentially dictated by the electronic character of the aryl substituent on the nitrogen atom of the parent thioisomuenchnone. However, further evolution of such cycloadducts into β-lactams or thiiranes is governed by steric effects to a large extent. Evidence for such interactions has been obtained by computing PM3-optimized diastereomeric transition structures in the reaction of a thioisomuenchnone with a chiral aliphatic aldehyde.