118508-99-9

Upstream product

• 115237-15-5 diethyl (-)-(4S,5S)-4,5-O-isopropylidene-4,5-dihydroxy-2,6-octadienedioate 
• 118508-97-7 (4S,5S)-4,5-O-isopropylidene-2E,6E-octadiene-1,4,5,8-tetraol 
• 100-39-0 benzyl bromide 
• 118508-98-8 (4S,5S)-4,5-O-isopropylidene-1,8-di-O-benzyl-2E,6E-octadiene-1,4,5,8-tetraol 

Downstream Products

• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 69152-87-0 4-benzyloxycrotonaldehyde 
• 118509-02-7 Acetic acid (R)-2-benzyloxy-1-hydroxymethyl-ethyl ester 
• 185025-19-8 Acetic acid (2E,5E)-(1R,4S)-4-acetoxy-7-benzyloxy-1-benzyloxymethyl-hepta-2,5-dienyl ester 
• 118509-01-6 (2R,7R)-2,7-di-O-acetyl-1,8-di-O-benzyl-23,5E-octadiene-1,2,7,8-tetraol 
• 104863-51-6 2-O-acetyl-3-O-benzyl-L-glyceraldehyde 
• 130878-20-5 (3E,5E)-(2R,7R)-1,8-Bis-benzyloxy-octa-3,5-diene-2,7-diol 
• 185025-17-6 Acetic acid (E)-(1S,2S)-5-benzyloxy-1-((E)-3-benzyloxy-propenyl)-2-(tert-butyl-diphenyl-silanyloxy)-pent-3-enyl ester 
• 16495-03-7 (S)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 118509-00-5 (4S,5S)-4,5-di-O-acetyl-1,8-di-O-benzyl-2E,6E-octadiene-1,4,5,8-tetraol 

Relevant academic research and scientific papers

SYNTHESIS OF AXIALLY DISSYMMETRIC 3,5-OCTADIENE FRAMEWORK WITH C2 CHIRALITY VIA PALLADIUM(II)-CATALYZED TWOFOLD SIGMATROPIC REARRANGEMENT

Palladium(II)-catalyzed sigmatropic rearrangement of (4R,5R)-4,5-(bisacetoxy)-1,8-(bisbenzyloxy)-2(E),6(E)-octadiene has proceeded convergently to give (2S,7S)-2,7-(bisacetoxy)-1,8-(bisbenzyloxy)-3(E),5(E)-octadiene, translating the original chirality completely to the migration termini, which constitutes a novel synthesis of optically pure 3,5-octadiene with C2 chirality.

Synthesis of chiral 3E,5E-octadiene-1,2R-7R,8-tetraol frameworks by means of palladium(II)-promoted hetero-Claisen rearrangement: Mechanistic aspect

A plausible mechanism has been proposed for the exclusive formation of symmetrical dienediol such as 1,6-bis(acetoxy)-2,4-diene in palladium(II)-promoted [3,3]sigmatropic rearrangement of 3,4-bis(acetoxy)-1,5-diene system. This mechanism referred to as migration-induced intramolecular dioxanium ion switching (MIDIS) process can reasonably explain why the vicinal acetoxy groups move from 3,4-position and not to 5,6- but two directionally to 1,6-position.