75648-24-7

Basic information

• Product Name: (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate
• Synonyms: (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate
• CAS NO: 75648-24-7
• Molecular Weight: 295.249
• Mol File: 75648-24-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate(75648-24-7)
• EPA Substance Registry System: (3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate(75648-24-7)

Safety Data

• Hazardous Substances Data: 75648-24-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 16106-20-0 isosorbide mononitrate 
• 65-85-0 benzoic acid 
• 652-67-5 Isosorbide 
• 56389-86-7 (3S,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl benzoate 

Downstream Products

• 16106-20-0 isosorbide mononitrate 

Relevant articles and documents

Synthesis of 2-[18F]Fluoro-2-deoxyisosorbide 5-mononitrate and Assessment of Its in vivo Biodistribution as Determined by Dynamic Positron Emission Tomography (PET)

Herein we disclose the synthesis of 2-fluoro-2-deoxyisosorbide 5-mononitrate (2F-IS-5MN), a fluorinated analogue of the commonly prescribed vasodilator isosorbide 5-mononitrate (IS-5MN). X-ray structural data for IS-5MN and its C2-epimeric congener IM-5MN are presented together with structural data for 2F-IS-5MN. Radioisotope labeling of 2F-IS-5MN has, for the first time, allowed observation of the in vivo biodistribution of this organic nitrate by means of dynamic positron emission tomography (PET) in wild-type mice. Visualization breakthrough: Herein we disclose the synthesis of a fluorinated analogue of the commonly prescribed vasodilator isosorbide 5-mononitrate (IS-5MN). Radioisotope labeling of 2F- IS-5MN has, for the first time, allowed observation of the in vivo biodistribution of this organic nitrate by means of dynamic positron emission tomography (PET) in wild-type mice.

Process for selectively producing isosorbide-5-nitrate

The present invention is related to a new process for selectively preparing isosorbide-5-nitrate (1.4-3.6-dianhydrosorbitol-5-nitrate) by subjecting isomannide (1.4-3.6-dianhydromannitol) in an organic solvent or an aqueous-organic reaction medium to reaction with the equivalent amount of an acid halogenide or the anhydride of a benzene or naphthalene sulfonic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen, of a perfluoro - lower alkane-sulfonic acid, of a lower alkanesulfonic acid or of a perfluoro - lower - alkanoic acid or with the equivalent amount of an acid halogenide of a carbamic acid or of sulphurous acid; subjecting the resulting isomannide-2-ester in the presence of a solvent and possibly with heating, to reaction with an alkali metal salt or an ammonium salt of a benzoic acid possibly substituted by lower alkyl, lower alkoxy and/or halogen or of a lower alkanoic acid; converting the hydroxy group in the 5-position of the resulting isosorbide-2-ester into the nitric acid ester group in manners known per se by reaction with nitric acid; and subjecting the resulting isosorbide-2-ester-5-nitrate to selective hydrolysis and/or reesterification in an organic or aqueous-organic solvent with an alkali metal hydroxide in manners known per se.