345891-86-3

Upstream product

• 345891-84-1 (E)-1-tributylstannyl-3,3-di(benzyloxy)prop-1-ene 
• 677-22-5 tert-butylmagnesium chloride 
• 345891-84-1 3,3-dibenzoyloxy-1-tributylstannylprop-1-ene 
• 142771-86-6 (CH₃)3C^(1-)*Cu⁽¹⁺⁾*CN^(1-)*Mg⁽²⁺⁾*Cl^(1-)=(CH₃)3CCu(CN)MgCl 

Downstream Products

• 51755-02-3 (2R,3S,4R)-2-Benzyloxy-3,4,5-trihydroxy-pentanal 
• 70797-88-5 (2R,3R,4R)-2-Benzyloxy-3,4,5-trihydroxy-pentanal 
• 884484-13-3 O²-Benzyl-arabinose 
• 345892-01-5 (E)-(1R,2R)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 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 
• 345891-96-5 (E)-(1S,2R)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 
• 345891-99-8 (E)-(1S,2S)-2-Benzyloxy-1-(R)-1,4-dioxa-spiro[4.5]dec-2-yl-5,5-dimethyl-hex-3-en-1-ol 

Relevant academic research and scientific papers

Preparation of α-substituted γ-alkoxyallylstannanes from β-tributylstannyl acrolein acetals: Scope of the method and primary rationalization of the obtained results

α-Substituted γ-alkoxyallylstannanes were obtained from β-tributylstannyl acrolein acetals when reacted with lower order magnesium cyanocuprates in the presence of boron trifluoride at low temperature. In the case of n-alkylcyanocuprates an anti SN2′ substitution on a cisoid conformation appears to be the main reaction pathway. However, subtle competitions with other mechanisms may occur depending on the experimental conditions, on the reagents or on the substrates. These drawbacks constitute limitations for the use of the method especially when enantioenriched α-substituted γ-alkoxyallylstannanes are desired.

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.