51755-02-3

Upstream product

• 345891-86-3 (Z)-1-benzyloxy-3-tributylstannyl-4,4-dimethylpent-1-ene 
• 345891-97-6 (E)-(1R,2S)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 

Downstream Products

• 58-86-6 D-xylose 

Relevant academic research and scientific papers

Reactivity of γ-benzyloxyallyltins with cyclohexylidene glyceraldehydes

Benzyloxyallyltributyltins were obtained in 50-80% yield by SN2′ reaction of alkyl-cyanocuprates with 3,3-dibenzyloxy-1-tributylstannylprop-1-ene in the presence of boron trifluoride. They reacted with cyclohexylidene glyceraldehyde in the presence of different Lewis acids and the obtained diastereomeric adducts were unambiguously identified after an ozonolysis/deprotection sequence by comparison with authentic aldopentoses. The mechanisms are briefly discussed as well as the relationship of the configuration of the reagents to the selectivity of the allylstannation reaction.