201857-82-1

Upstream product

• 71038-25-0 methyl (E)-3-(3,4-bis(benzyloxy)phenyl)acrylate 
• 3843-74-1 Methyl caffeate 
• 331-39-5 caffeic acid 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 203571-40-8 3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester 

Downstream Products

• 1253890-79-7 (-)-(2S,3R,4R)-2-(3',4'-dihydroxyphenyl)tetrahydrofuran-3,4-diol 
• 1253890-80-0 (-)-(2S,3S,4R)-2-(3',4'-diacetoxyphenyl)-3,4-diacetoxytetrahydrofuran 

Relevant academic research and scientific papers

Stereoselective synthesis of peracetylated (?)-gloeosporiol via acid catalysed intramolecular etherification

A simple and an efficient strategy have been developed for the stereoselective synthesis of peracetylated (?)-gloeosporiol by acid catalysed cyclisation from the commercially available starting materials.

Asymmetric Synthesis of a Series of Chiral AB2 Monomers for Dendrimer Construction

Efficient preparation of a series of four chiral, nonracemic AB2 monomers suitable for the construction of dendrimers is presented. Monomers 1-4 possess the common structural features of a diphenolic moiety and a benzylic or aliphatic hydroxyl which render these molecules suitable for convergent dendrimer synthesis. The same basic, high-yielding, five-step sequence is employed for 1-4. Stilbene derivatives 13 and 14 are prepared by a Horner-Wadsworth-Emmons modified Wittig reaction between 3,5- or 3,4-bis(benzyloxy)benzaldehyde (8 and 10) and an ester-substituted benzylphosphonate (11 or 12). Cinnamate derivatives 21 and 22 are prepared similarly from 8 and 10 and triethyl phosphonoacetate. Chirality is introduced in the form of a 1,2-diol unit by Sharpless asymmetric dihydroxylation (AD) (>97% ee in all cases). Protection of the 1,2-diols as their acetonide derivatives provides dioxolane intermediates 17, 18, 25, and 26. Reduction of the ester groups followed by hydrogenolysis of the benzyl ethers yields AB2 monomers 1-4 in 57-67% overall yield from 8 and 10.