151378-29-9

Basic information

• Product Name: Ethanone, 1-(tetrahydro-5-hydroxy-4-methyl-3-furanyl)- (9CI)
• Synonyms: Ethanone, 1-(tetrahydro-5-hydroxy-4-methyl-3-furanyl)- (9CI)
• CAS NO: 151378-29-9
• Molecular Formula: C₇H₁₂O₃
• Molecular Weight: 144.16838
• Product Categories: ACETYLGROUP
• Mol File: 151378-29-9.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(tetrahydro-5-hydroxy-4-methyl-3-furanyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(tetrahydro-5-hydroxy-4-methyl-3-furanyl)- (9CI)(151378-29-9)
• EPA Substance Registry System: Ethanone, 1-(tetrahydro-5-hydroxy-4-methyl-3-furanyl)- (9CI)(151378-29-9)

Safety Data

• Hazardous Substances Data: 151378-29-9(Hazardous Substances Data)

Upstream product

• 127-09-3 sodium acetate 
• 69544-17-8 (2R,3S,4R,5Ξ)-4,5-dihydroxy-3-hydroxymethyl-2,4-dimethyl-hexanal (R)-1->4-cyclohemiacetal 
• 69544-16-7 (3R)-4t-acetoxymethyl-5c-acetyl-3r,5t-dimethyl-dihydro-furan-2-one 
• 114286-20-3 (+)-(2R,3S,4R)-4-acetyl-2-benzyloxy-3-methyltetrahydrofuran 
• 104322-42-1 (-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde 
• 123284-71-9 (+)-(2S,3S)-2-benzyloxy-4-<(tert-butyldimethylsilyloxy)methylene>-3-methyltetrahydrofuran 
• 113466-39-0 (+)-(2R,3S,4SR)-2-benzyloxy-4-formyl-3-methyltetrahydrofuran 
• 113466-43-6 (2R,3S,4SR)-2-benzyloxy-4-(1-hydroxyethyl)-3-methyltetrahydrofuran 
• 113466-48-1 (-)-(2S,3R,4R)-4-acetyl-2-benzyloxy-3-methyltetrahydrofuran 
• 104322-41-0 (+)-(2R)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde 
• 123284-70-8 (-)-(2R,3R)-2-benzyloxy-4-<(tert-butyldimethylsilyloxy)methylene>-3-methyltetrahydrofuran 
• 113466-39-0 (-)-(2S,3R,4RS)-2-benzyloxy-4-formyl-3-methyltetrahydrofuran 
• 113466-43-6 1-((4R,5S)-5-Benzyloxy-4-methyl-tetrahydro-furan-3-yl)-ethanol 
• 113466-50-5 (+)-(2R,3S,4S)-4-acetyl-2-benzyloxy-3-methyltetrahydrofuran 

Relevant articles and documents

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Diastereoselective radical cyclization of bromoacetals: Efficient synthesis of (±)-botryodiplodin

A stereoselective synthesis of (±)-botryodiplodin is presented. The key reaction is a radical cyclization of a bromoacetal (Ueno-Stork reaction). The stereogenic acetal center has been used to control the stereoselectivity of the process: the difficulty in controlling the stereochemistry at C(3) of the tetrahydrofuran moiety during the cyclization step has been overcome by a double one-pot reduction procedure starting from a gem-dibromide.

Synthesis of (±)- and (-)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals

Three different routes for the stereoselective synthesis of botryodiplodin have been investigated. The intramolecular allylation of acetals proved to be unsatisfactory due to unstable intermediates and poor stereocontrol. Zard intramolecular radical allyl

Acyclic Stereoselection in the Ortho Ester Claisen Rearrangement

The ortho ester Claisen rearrangement of trisubstituted allylic alcohols exhibits significant levels of diastereoselection. In E allylic alcohols, a 1,3-diaxial interaction develops in the chairlike transition state leading to the anti isomer, rendering the reaction syn selective by a factor of 3-5 to 1. In Z allylic alcohols, the 1,3-diaxial interaction develops in the transition state leading to the syn isomer, generating an anti:syn selectivity of 6-15 to 1. The relative stereochemistry of the syn isomer was confirmed independently by the synthesis of the mycotoxin botryodiplodin.