505081-54-9

Basic information

• Product Name: 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-, (2R,3R,7S,7aR)- (9CI)
• Synonyms: 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-, (2R,3R,7S,7aR)- (9CI)
• CAS NO: 505081-54-9
• Molecular Formula: C11H14O4
• Molecular Weight: 210.22646
• Product Categories: ALCOHOL
• Mol File: 505081-54-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-, (2R,3R,7S,7aR)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-, (2R,3R,7S,7aR)- (9CI)(505081-54-9)
• EPA Substance Registry System: 5H-Furo[3,4-b]pyran-5-one, 2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-, (2R,3R,7S,7aR)- (9CI)(505081-54-9)

Safety Data

• Hazardous Substances Data: 505081-54-9(Hazardous Substances Data)

Upstream product

• 17087-84-2 (3aS,4R,6R,6aS)-4-chloro-6-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 505081-54-9 (+/-)-(2R,3R,7R,7aR)-2,3,7,7a-tetrahydro-3-hydroxy-7-methyl-2-(1E)-1-propenyl-5H-furo[3,4-b]pyran-5-one 
• 683239-68-1 (+/-)-(2R,7R,7aR)-7,7a-dihydro-7-methyl-2-(1E)-1-propenyl-5H-furo[3,4-b]pyran-3,5(2H)-dione 
• 20432-44-4 (2E,4E/Z)-2,4-hexadienal 
• 38996-24-6 (4R,5R)-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 
• 502971-48-4 2,5-dideoxy-2-[(1S,2E,4E)-1-hydroxy-2,4-hexadienyl]-L-arabinonic acid γ-lactone 
• 98512-76-6 (-)-(4R,5S)-dihydro-4-hydroxy-5-methyl-2(3H)-furanone 
• 502971-07-5 [2R-(2α,3β,4α,4aα,7β,7aβ)]-hexahydro-4-hydroxy-3-iodo-7-methyl-2-(1E-propenyl)-5H-furo[3,4-b]pyran-5-one 

Relevant articles and documents

Synthesis of (-)-TAN-2483A. Revision of the structures and syntheses of (±)-FD-211 (waol A)and (±)-FD-212 (waol B)

(Matrix presented) The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483 A (5). Aldol reaction of 10b(c) with 2,4-hexadienal (11) affords 9b(c), which is subjected to iodoetherification with bis(sym-collidine)IPF6 to p

Total Synthesis and Bioactivity Studies of Fungal Metabolite (-)-TAN-2483B

The first total synthesis of (-)-TAN-2483B, a fungal metabolite possessing a densely functionalized furo[3,4-b]pyran-5-one framework, is achieved in 14 steps from d-mannose. Generation of the 2,6-trans-pyran is by cyclopropane ring expansion followed by α-selective alkynylation. Julia-Kocienski olefination introduces the E-propenyl side chain. Alkyne functionalization and carbonylation stereoselectively establish the bicyclic core of (-)-TAN-2483B. Inhibition of kinases Btk and Bmx, bacterial priority pathogens, and cytokine production in splenocytes indicates promising therapeutic potential.

Syntheses of (-)-TAN-2483A, (-)-massarilactone B, and the fusidilactone B ring system. Revision of the structures of and syntheses of (±)-Waol A (FD-211) and (±)-Waol B (FD-212)

The structure of waol A has been revised from 1 to 6, the vinylogue of TAN-2483A (5). Aldol reaction of hydroxybutanolides 13b,c with 2,4-hexadienal affords 12b,c, which are subjected to iodoetherification with bis(sym-collidine)IPF6 to provide