89358-85-0

Basic information

• Product Name: ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate
• CAS NO: 89358-85-0
• Molecular Weight: 412.911
• Mol File: 89358-85-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate(89358-85-0)
• EPA Substance Registry System: ethyl 3C-(4-chlorophenyl)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-manno-heptonate(89358-85-0)

Safety Data

• Hazardous Substances Data: 89358-85-0(Hazardous Substances Data)

Upstream product

• 13039-93-5 2,2:4,5-di-O-isopropylidene-D-arabinose 
• 65391-47-1 (E)-ethyl 3-((4R,5S)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 7270-47-5 4-chlorophenylmagnesium iodide 

Downstream Products

• 89359-15-9 dimethyl (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioate 
• 89359-12-6 (+)-(S)-2-(4-chlorophenyl)butane-1,4-dioic acid 
• 89359-13-7 3-(4-chlorophenyl)-4-hydroxybutyro-1,4-lactone 
• 89359-16-0 (S)-β-(4-chlorophenyl)-γ-butyrolactone 
• 89358-94-1 3C-(4-chlorophenyl)-2,3-dideoxy-D-manno-heptono-1,4-lactone 

Relevant articles and documents

Asymmetric Synthesis. Part 6. Copper Salt promoted Grignard Reagent Additions to Ethyl 2,3-Dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate and subsequent Formation of Optically Active 2-Alkyl (or Aryl) Butane-1,4-dioic Acids and Butyro-1,4-lactones

The copper-salt promoted 1,4-additions of aryl and t-butyl Grignard reagents to ethyl 2,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-trans-hept-2-enonate are highly stereoselective yielding products with the D-manno-configuration.In contrast isopropyl and ethyl Grignarg reagents give products preponderantly with the D-gluco-configuration.Cyclohexylmagnesium bromide does not react stereoselectively but gives a 55:45 mixture of the D-gluco- and D-manno-isomers.Controlled degradation of the carbohydrate molecule affords 2-aryl (alkyl) butane-1,4-dioic acids and 3-aryl (alkyl)-butyro-1,4-lactones.The enantiomeric purity of these products is established by reference to known products or by use of optically active n.m.r. shift reagents.