120686-95-5

Upstream product

• 2871-84-3 (R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one 
• 185675-42-7 Oxalic acid benzyl ester (R)-benzyloxycarbonyl-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl ester 
• 93367-08-9 Kalium-<4S-(R*,S*)>-α-hydroxy-2,2-dimethyl-1,3-dioxolan-4-acetat 
• 100-39-0 benzyl bromide 

Downstream Products

• 91274-05-4 (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 
• 100-51-6 benzyl alcohol 

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.

Chiral Lactols, VIII - A Way for the Asymmetric Induction in the Formation of Sugars

The substituted glycol aldehyde 4 which bears an enantiomerically pure acetal-type protective group exhibiting the configuration of an α-L-sugar at the acetal centre is subjected to aldolization under basic conditions.The resulting products are reduced and characterized by comparison with reference compounds of known absolute configuration.L-Sugars are formed preferentially with L-erythrose being the main product.