144895-69-2

Upstream product

• 144895-66-9 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2-oxo-1,3-dioxolan-4-yl)acrylate 
• 98-80-6 phenylboronic acid 
• 69152-87-0 4-benzyloxycrotonaldehyde 
• 124755-24-4 ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 
• 848566-19-8 (E,4S,5S)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 
• 90661-39-5 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 81028-12-8 (4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde 
• 144895-64-7 (E)-3-((4S,5S)-5-Benzyloxymethyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-acrylic acid ethyl ester 
• 917-54-4 methyllithium 

Downstream Products

• 848566-32-5 (E,4R,5R)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 
• 848566-19-8 (E,4S,5S)-ethyl 6-(benzyloxy)-4,5-dihydroxyhex-2-enoate 
• 1012054-47-5 (-)-(E)-ethyl 5-(benzyloxymethyl)hept-3-enoate 
• 1409973-20-1 C₂₆H₄₀O₃Si 
• 852611-12-2 (2S,3S,4R,5S)-ethyl 4-(4-methoxyphenoxy)-6-(benzyloxy)-2,3,5-trihydroxyhexanoate 
• 852611-09-7 (E,4S,5S)-ethyl 4-(4-methoxyphenoxy)-6-(benzyloxy)-5-hydroxyhex-2-enoate 
• 852611-21-3 (3S,4S,5S,6S)-5-(4-methoxyphenoxy)-6-((benzyloxy)methyl)-tetrahydro-3,4-dihydroxypyran-2-one 
• 215544-02-8 (2S,3S)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxypropanoate 
• 144895-66-9 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2-oxo-1,3-dioxolan-4-yl)acrylate 
• 90661-39-5 (E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate 
• 848566-38-1 (2R,3S,5R)-ethyl 6-(benzyloxy)-2,3,5-trihydroxy-hexanoate 
• 848566-36-9 (2S,3R,5R)-ethyl 6-(benzyloxy)-2,3,5-trihydroxy-hexanoate 
• 848566-33-6 (3R,4R,5S)-5-(2'-benzyloxy-(1'R)-1'-hydroxy-ethyl)-3,4-dihydroxy-dihydro-furan-2(3H)-one 

Relevant academic research and scientific papers

A de novo asymmetric approach to achiral deoxy-melodorinol analogues

A short and highly efficient route to deoxy-Melodorinol analogues has been developed. The key to the overall transformation is the use of an enantioselective Sharpless asymmetric dihydroxylation of an (Z,E)-dienoate to control the regioselectivity of the dihydroxylation reaction and a Mitsunobu elimination reaction to control the E-stereochemistry of the,δ-double bond. The highly efficient synthesis stereoselectively prepared four analogues in 3 steps from 4-substituted crotonaldehydes.

De novo asymmetric syntheses of D- and L-talose via an iterative dihydroxylation of dienoates

A short and highly efficient route to D- and L-tafo-γ-lactones has been developed. The key transformation was the sequential osmium-catalyzed bis-dihydroxylation reaction of substituted 2,4-dienoates. When the first dihydroxylation reaction is performed o

Palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols with double inversion of the configuration

A palladium-catalyzed stereospecific epoxide-opening reaction of γ,δ-epoxy-α,β-unsaturated esters with an alkylboronic acid leading to γ,δ-vicinal diols is described, which proceeds with retention of the configuration, i.e., via two consecutive SN/s

Addition of Organocopper Reagents to Cyclic Sulfites or Carbonates of γ,δ-Dihydroxy (E)-α,β-Enoates

Reaction of cyclic sulfites or carbonates of γ,δ-dihydroxy (E)-α,β-enoates with R2Cu(CN)Li2, BF3; RCu(CN)Li, BF3 (R=Me-, n-Bu-) afforded either diastereoselective SN2' products or reductive elimination product depending on reaction conditions.Addition of R2Cu(CN)Li2, BF3 (R=Me-, n-Bu-) to cyclic sulfite (1) or cyclic carbonate (3) (inverse addition) afforded highly regio-, (E)-stereo- and diastereoselectivity α-alkylation products (6 and 8).By using this methodology, (2S, 5S)-trans-2-methyl-5-hexanolide, the pheromone of the carpenter bee Xylocopa hirutissima was synthesized.