256221-89-3

Basic information

• Product Name: (4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one
• CAS NO: 256221-89-3
• Molecular Weight: 186.208
• Mol File: 256221-89-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one(256221-89-3)
• EPA Substance Registry System: (4S,4aS,7S,7aR)-4-Hydroxy-7-hydroxymethyl-hexahydro-cyclopenta[c]pyran-3-one(256221-89-3)

Safety Data

• Hazardous Substances Data: 256221-89-3(Hazardous Substances Data)

Upstream product

• 256221-80-4 4',6'-isopropylidene-10-O-(1-methyl-1-methoxyethyl)-geniposide 

Downstream Products

• 256221-98-4 9-((1R,2S,3S)-2,3-Bis-benzyloxymethyl-cyclopentylmethyl)-9H-purin-6-ylamine 
• 256221-95-1 C₂₃H₂₆O₆ 
• 256221-92-8 (S)-1-((1S,2R,3S)-2,3-Bis-benzyloxymethyl-cyclopentyl)-ethane-1,2-diol 
• 256221-96-2 C₂₂H₂₄O₅ 
• 256221-94-0 ((1R,2S,3S)-2,3-Bis-benzyloxymethyl-cyclopentyl)-methanol 
• 256221-90-6 (S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol 

Relevant articles and documents

Stereoselective hydrogenation and ozonolysis of iridoids. Conversion into carbocyclic nucleoside analogues

Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1- methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).