99883-96-2

Upstream product

• 138722-32-4 Carbonic acid (E)-(R)-1-benzyloxymethyl-3-trimethylsilanyl-allyl ester methyl ester 
• 138810-05-6 (E,2R)-1-O-benzyl-4-trimethylsilylbut-3-ene-1,2-diol 
• 119046-51-4 (2S,3S,4S)-1-O-benzyl-3,4-epoxy-4-(trimethylsilyl)butane-1,2-diol 
• 99883-94-0 (2S,3S)-4-(benzyloxy)-1,1-dimethoxy-2,3-epoxybutane 

Relevant academic research and scientific papers

A New Iterative Route to Optically Active Polyols Using α-Alkoxy Silanes as Key Intermediates

A new iterative and modular strategy which is applicable to the synthesis of any enantiomers and diastereomers of straight chain 1,n-polyols has been developed utilizing electrochemical oxidation of α-alkoxy silanes.

Selective Transformations of 2,3-Epoxy Alcohols and Related Derivatives. Strategies for Nucleophilic Attack at Carbon-3 or Carbon-2

The ring-opening reactions of 2,3-epoxy alcohols 1 under nonisomerizing conditions were investigated.There is an inherent tendency for ring-opening at the C-3 position of 1 due to an electronic effect of the C-1 hydroxyl group.Since the hydroxyl group is a relatively weak inductively electron-withdrawing group, C-3 selective ring-opening reactions are observed only with certain simple 2,3-epoxy alcohols.Since an electronic effect of the C-1 hydroxyl group was found to promote ring-opening at the C-3-position of 1, the ring-opening reactions of 2,3-epoxy acetals and 2,3-epoxy amides were also explored, under the assumption that the acetal and amide groups might promote C-3 opening more strongly than the hydroxyl group.As expected, 2,3-epoxy acetals were opened with various nucleophiles exclusively at the C-3 position.However, the ring-opening reactions of 2,3-epoxy amides exhibited variable behavior, affording the C-3 ring-opened products with Mg(N3)2 and the C-2 ring-opened products with PhSK.