127940-36-7

Basic information

• Product Name: (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one
• Synonyms: (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one
• CAS NO: 127940-36-7
• Molecular Weight: 214.218
• Mol File: 127940-36-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one(127940-36-7)
• EPA Substance Registry System: (5R)-5-((S)-[((R)-2,2-dimethyl-1,3-dioxolan-4-yl)hydroxymethyl])-5H-furan-2-one(127940-36-7)

Safety Data

• Hazardous Substances Data: 127940-36-7(Hazardous Substances Data)

Upstream product

• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 70606-00-7 (R)-tetrahydro-5-oxo-2-furancarbaldehyde 
• 113299-30-2 4a-carba-β-L-lyxofuranose 
• 105265-95-0 (1S,2S,3S,4S)-4-(hydroxymethyl)cyclopentane-1,2,3-triol 
• 118013-56-2 (1R,2S,3R,4R)-4-(hydroxymethyl)cyclopentae-1,2,3-triol 
• 305384-19-4 (1R,2S,3R,4S,5R)-2,3-di-O-(tert-butyldimethylsilanyl)-4-O-(triethylsilanyl)-5-hydroxymethylcyclohexane-1,2,3,4-tetrol 

Relevant articles and documents

THE FOUR-CARBON ELONGATION OF THREE-CARBON CHIRAL SYNTHONS USING 2-(TRIMETHYLSILOXY)FURAN: HIGHLY STEREOCONTROLLED ENTRY TO ENANTIOMERICALLY PURE SEVEN-CARBON α,β-UNSATURATED 2,3-DIDEOXYALDONOLACTONES

The BF3-promoted addition of 2-(trimethylsiloxy)furan to three carbon synthons derived from D- and L-glyceraldehyde, D- and L-serinal, and imines thereof furnishes C7 α,β-unsaturated 2,3-dideoxy-aldonolactone derivatives in high yield, with very high level of diastereoselection.In all the cases, compounds having 4,5-threo:5,6-erythro relative stereodisposition preferentially emerge from the reactions, accompanied by only marginal amounts of 4,5-erythro:5,6-threo epimers.An empirical rule for the rapid assignment of the configuration at C-4 (γ-carbon) of γ-substituted unsaturated and saturated β-butyrolactones is given, based upon the sign of the optical rotation values.