495397-80-3

Basic information

• Product Name: Bicyclo[3.1.0]hexane-2,3,4-triol, 1-(hydroxymethyl)-, (1S,2S,3R,4R,5R)- (9CI)
• Synonyms: Bicyclo[3.1.0]hexane-2,3,4-triol, 1-(hydroxymethyl)-, (1S,2S,3R,4R,5R)- (9CI)
• CAS NO: 495397-80-3
• Molecular Formula: C₇H₁₂O₄
• Molecular Weight: 160.16778
• Product Categories: CYCLOPENTANE;ALCOHOL
• Mol File: 495397-80-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bicyclo[3.1.0]hexane-2,3,4-triol, 1-(hydroxymethyl)-, (1S,2S,3R,4R,5R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Bicyclo[3.1.0]hexane-2,3,4-triol, 1-(hydroxymethyl)-, (1S,2S,3R,4R,5R)- (9CI)(495397-80-3)
• EPA Substance Registry System: Bicyclo[3.1.0]hexane-2,3,4-triol, 1-(hydroxymethyl)-, (1S,2S,3R,4R,5R)- (9CI)(495397-80-3)

Safety Data

• Hazardous Substances Data: 495397-80-3(Hazardous Substances Data)

Upstream product

• 389626-29-3 (1S,2S,3R,4R,5R)-1-(hydroxymethyl)-3,4-isopropylenedioxybicyclo[3.1.0]hexane-2,3,4-triol 
• 155792-02-2 ethyl (1R,4R)-8,8-dimethyl-5-oxo-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate 
• 1026649-94-4 C₁₈H₂₁IO₅ 
• 495397-74-5 ethyl (1R,4R)-5-hydroxy-8,8-dimethyl-7,9-dioxatricyclo[4.3.0.0^[2,4]]nonane-4-carboxylate 
• 155792-01-1 ethyl 2-diazo-3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate 
• 155792-00-0 ethyl 3-(5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl)-3-oxopropanoate 

Downstream Products

• 389626-35-1 (1S,2S,3R,4R,5R)-1-[(trityloxy)methyl]bicyclo[3.1.0]hexane-2,3,4-triol 

Relevant articles and documents

Bicyclo[3.1.0]hexanes from sugar-derived diazo compounds and iodonium ylides. Diastereocontrol and synthetic applications

The CuI and Rh2(OAc)4 catalyzed decomposition of ethyl 2-diazo-4,5-isopropylidenedioxy-3-oxo-6-heptenoate results in intramolecular cyclopropanation products with opposite diastereoselectivity. In contrast, decomposition of the respective iodonium ylide can proceed without catalysts to give the cyclopropanation products with diastereoselectivity unchangeable by the presence of CuI and Rh2(OAc)4, revealing thus, that in this particular case the reaction is an electrophilic addition of the iodonium center to the double bond. The synthetic importance of these reactions has been demonstrated by preparing a number of precursors of cyclopentyl, cyclopropyl and bicyclo[3.1.0]hexyl antiviral carbocyclic nucleosides.

Carbocyclic nucleoside precursors by intramolecular cyclopropanation of sugar-derived diazo compounds

Bicyclo[3.1.0]hexane derivatives, selectively prepared by intramolecular cyclopropanation of sugar-derived unsaturated diazo compounds, are common precursors for the sugar moiety of cyclopentane, cyclopropane and bicyclo[3.1.0]hexane nucleosides, such as aristeromycin, the carbocyclic analogue of neplanocin C and the nucleoside A-5021.