136767-82-3

Upstream product

• 100-39-0 benzyl bromide 
• 15042-01-0 5,6-O-isopropylidene-L-ascorbic acid 
• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 
• 89-65-6 isoascorbic acid 
• 185675-50-7 (R)-3,4-Bis-benzyloxy-5-((2R,4S)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 99663-32-8 (2R)-3,4-dibenzyloxy-2-[(1S)-1,2-dihydroxyethyl]-2H-furan-5-one 
• 114184-95-1 (R)-3,4-Dihydroxy-5-((R)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-53-0 (R)-3,4-Bis-benzyloxy-5-((2S,4R)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-54-1 (R)-3,4-Bis-benzyloxy-5-((2R,4R)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 185675-51-8 (R)-3,4-Bis-benzyloxy-5-((2S,4S)-2-phenyl-[1,3]dioxolan-4-yl)-5H-furan-2-one 
• 122046-90-6 O²,O³-dibenzyl-O⁵,O⁶-isopropyliden-L-ascorbic acid 

Relevant academic research and scientific papers

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.