874896-62-5

Upstream product

• 874896-58-9 (4S,E)-ethyl 4-(benzyloxy)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate 
• 340699-28-7 ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 100-39-0 benzyl bromide 

Downstream Products

• 874896-64-7 ethyl (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanoate 
• 874896-66-9 (2R,3S,4R,5S)-2,3:5,6-di(O-isopropylidene)-4-O-benzyl-2,3,4,5,6-pentahydroxyhexanal 

Relevant academic research and scientific papers

Synthesis of C1–C11 eribulin fragment and its diastereomeric analogues

A practical stereoselective synthesis of the central C1–C10 fragment of eribulin and its two diastereomeric analogues is developed. Our approach relied on the use of L-ascorbic acid as the starting material which allowed accessing a key intermediate with a syn diol moiety (C9 and C10 of eribulin) and a carboxylic ester group. A functionalized six membered lactone having several required hydroxyl groups was then obtained. In a number of steps, the lactone was converted to an intermediate for our key oxa-Michael reaction. A regio- and stereocontrolled intramolecular oxa-Michael reaction completed the synthesis of the C1–11 fragment having a trans-fused tetrahydropyrans with the exact stereochemistry of various hydroxyl groups, as in eribulin.

Diastereoselective synthesis of all eight L-hexoses from L-ascorbic acid

A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy- α,β-unsaturated esters C via the int