89678-08-0

Basic information

• Product Name: 6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone
• Synonyms: 6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone;RKMPAOIJAUYXRD-UHFFFAOYSA-N
• CAS NO: 89678-08-0
• Molecular Formula: C₇H₇IO₃
• Molecular Weight: 266.03315
• Product Categories: Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 89678-08-0.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Acetonitrile, Methanol
• CAS DataBase Reference: 6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone(89678-08-0)
• EPA Substance Registry System: 6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone(89678-08-0)

Safety Data

• Hazardous Substances Data: 89678-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Hydroxy-5-iodo-7-oxabicyclo[2.2.1]heptane-2-carboxylic Acid γ-Lactone is used as an intermediate in the synthesis of neuraminidase inhibitors for the treatment of influenza and other viral infections. Its unique structure and functional groups make it a valuable component in the development of these antiviral medications, contributing to their efficacy and potency in combating viral replication and spread.

Upstream product

• 24363-23-3 (+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid 
• 24363-23-3 7-oxabicyclo[2.2.1]hept-2-ene-endo-5-carboxylic acid 
• 84752-05-6 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic chloride 
• 110-00-9 furan 
• 814-68-6 acryloyl chloride 
• 21987-33-7 7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic acid,methyl ester 
• 563-63-3 silver(I) acetate 
• 90760-55-7 (1R,2R,4S)-7-oxabicyclo<2.2.1>hept-5-ene-2-carboxylic acid 

Downstream Products

• 494195-98-1 (1S,5S,6R)-5-acetoxy-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-ene 
• 635678-63-6 (1R,2S,4S,5R,7R)-7-hydroxymethyl-3,8-dioxatricyclo[5.1.0.0^2,4]octan-5-ol 
• 635678-66-9 (2R,3R,4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-cyclohex-5-en-1-one 
• 78844-86-7 rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 
• 78844-86-7 methyl 3(R),4(R)-epoxy-5(R)-hydroxy-1-cyclohexene-1-carboxylate 
• 141276-72-4 1,4,6-tri-O-acetyl-2-deoxy-3-O-methoxymethyl-5a-carba-α-L-lyxo-hexopyranose 
• 141276-70-2 3,4,6-tri-O-acetyl-2-deoxy-5a-carba-β-L-xylo-hexopyranosyl chloride 
• 141276-71-3 1,4,6-tri-O-acetyl-2-deoxy-5a-carba-α-L-lyxo-hexopyranose 

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A Prevost-type reaction under "wet" conditions upon the O-t-butyl-dimethylsilyl derivative of (+/-)-methyl 5β-hydroxycyclohexa-1,3-dienoate gives (+/-)-methyl 3α-acetoxy-4β-hydroxy-5β-t-butyldimethylsilyloxycyclohexene which may be readily deprotected to afford (+/-)-methyl shikimate in very high yield.Less selectivity is observed in a similar reaction upon the parent alcohol and when this compound is reacted under dry conditions the major product is (+/-)-methyl 4β,5β-epoxy-3β-acetoxycyclohexenoate.An analysis of Prevost reactions with exo and endo methyl 7-oxabicyclohept-5-en-2-oate is also described.