601490-94-2

Upstream product

• 115520-88-2 methyl 2,3,4-tri-O-benzyl-6,7-dideoxy-oct-6(E)-eno-α-D-manno-1,5-pyranoside 
• 601490-93-1 methyl 2,3,4-tri-O-benzyl-6,7,8-trideoxy-8-bromo-oct-6(E)-eno-α-D-manno-1,5-pyranoside 

Downstream Products

• 343312-81-2 Tributyl-[(S)-1-((2S,3S,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-allyl]-stannane 

Relevant academic research and scientific papers

Synthesis and thermal stability of secondary sugar allyltin derivatives

Reaction of sugar allylic mesylates with tri-n-butyltin cuprate affords the primary and secondary allyltin derivatives: Sug-CH=CH-CH2SnBu3 and Sug-CH(SnBu3)-CH=CH2 with the latter predominating. The SN2′ addition led almost exclusively to one isomer with the S configuration at the newly created stereogenic center. Only traces of the opposite R isomer were formed. Both stereoisomers of secondary allyltins decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The main S isomer gives the dienoaldehyde CH2=CH-CH=CH-[(CHOR)3]-CHO with the cis geometry across the internal double bond. The minor R isomer provides the trans dienoaldehyde under the same conditions. These results strongly suggest the concerted (E2) mechanism of thermal decomposition of secondary sugar allyltin derivatives.