185675-57-4

Usage

Class

Furanone

Molecular structure

Contains a furanone ring with two phenylmethoxy groups and a hydroxyethylidene group attached

Configuration

The (Z)designation indicates that the double bond in the hydroxyethylidene group is in a cis configuration

Potential applications

Flavoring agent, fragrance ingredient, and in organic synthesis

Value

Unique structure and properties make it valuable for research and industrial use

Upstream product

• 107-10-8 propylamine 
• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 
• 99663-32-8 (2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 109-73-9 N-butylamine 
• 104040-11-1 2,3-O,O-dibenzyl-4,5-didehydro-5,6-O,O-ditosyl-L-ascorbic acid 
• 127-09-3 sodium acetate 

Downstream Products

• 1617539-91-9 Z-⁽²⁾-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidine)ethyl 4-methylbenzenesulfonate 
• 1617539-88-4 C₄₀H₄₂N₄O₄ 
• 1617539-90-8 (Z)-3,4-bis(benzyloxy)-1-octyl-5-(2-(4-(pyridin-2-yl)-1H-1,2,3-triazol-1-yl)ethylidene)-1H-pyrrol-2(5H)-one 
• 1617539-84-0 5-(2-(4-benzyl-1H-1,2,3-triazol-1-yl)ethyl)-3,4-bis(benzyloxy)-5-hydroxy-1H-pyrrol-2(5H)-one 
• 1617539-81-7 3,4-bis(benzyloxy)-5-hydroxy-5-(2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl)-1H-pyrrol-2(5H)-one 
• 1617539-83-9 3,4-bis(benzyloxy)-5-hydroxy-5-(2-(4-p-tolyl-1H-1,2,3-triazol-1-yl)ethyl)-1H-pyrrol-2(5H)-one 
• 1617539-85-1 3,4-bis(benzyloxy)-5-(2-(4-(4-tert-butylphenyl)-1H-1,2,3-triazol-1-yl)ethyl)-5-hydroxy-1H-pyrrol-2(5H)-one 
• 1617539-89-5 (Z)-3,4-bis(benzyloxy)-1-propyl-5-(2-(4-propyl-1H-1,2,3-triazol-1-yl)ethylidene)-1H-pyrrol-2(5H)-one 
• 1617539-59-9 (Z)-3,4-bis(benzyloxy)-5-(2-(4-propyl-1H-1,2,3-triazol-1-yl)ethylidene)furan-2(5H)-one 
• 1617539-60-2 (Z)-2,3-O,O-dibenzyl-6-(4-butyl-1,2,3-triazole-1-yl)-4,5-didehydro-5,6-dideoxy-L-ascorbic acid 
• 1617539-61-3 (Z)-3,4-bis(benzyloxy)-5-(2-(4-pentyl-1H-1,2,3-triazol-1-yl)ethylidene)furan-2(5H)-one 
• 1617539-65-7 C₂₆H₂₇N₃O₅ 
• 1617539-67-9 (Z)-5-(2-(4-benzyl-1H-1,2,3-triazol-1-yl)ethylidene)-3,4-bis(benzyloxy)furan-2(5H)-one 
• 1617539-69-1 (Z)-3,4-bis(benzyloxy)-5-(2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethylidene)furan-2(5H)-one 

Relevant academic research and scientific papers

L-Ascorbic acid in organic synthesis: DBU-catalysed one-pot synthesis of tetramic acid derivatives from 5,6-O-isopropylidene ascorbic acid

Reaction of 5,6-O-isopropylidene-2,3-bis-O-alkyl ascorbic acid with different amines in the presence of DBU at ambient temperature resulted in the formation of 3,4-bis-O-alkyl-1-alkyl-5-(2-hydroxy ethyl)-5-hydroxy-1,5- dihydropyrrol-2-ones in moderate yie

Synthesis, structural studies, and cytostatic evaluation of 5,6-di-O-modified L-ascorbic acid derivatives

The 5,6-di-O-tosylated derivative of L-ascorbic acid was synthesized by selective protection and deprotection of 2,3- and 5,6-dihydroxy functional groups involving 5,6-ditosylation in the final step, while the novel 6-acetoxy, 6-hydroxy, and 6-chloro deri

Organoalane-mediated isomerization of ascorbic and isoascorbic acid derivatives

Derivatives of L-ascorbic acid 2a, 10a/11a and D-isoascorbic acid 2b, 10b/11b, when treated with triisobutylaluminium, partly epimerize to give the corresponding derivatives of L-isoascorbic acid ent-2b, ent-10b or D-ascorbic acid ent-2a, ent-10a, ent-11a, respectively. Complete removal of the protecting groups is effected by hydrogenolysis of the benzylidene acetals ent-10 and ent-11a. This reaction leads to D-ascorbic acid ent-1a or L-isoascorbic acid ent-1b, respectively. Furthermore, the four acetonides 2 were converted by ozonolysis, transesterification and finally catalytic hydrogenation to the threonic and erythronic acid ketals 9. Copyright (C) Elsevier Science Ltd.