193603-90-6

Upstream product

• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 125287-97-0 methyl uronate 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 193553-77-4 2,3,4-tri-O-benzyl-5,6,7,8-tetradeoxy-5(E),7-dieno-oct-D-lyxitol xanthate 
• 202120-68-1 (E)-(3S,4S,5R)-3,4,5-Tris-benzyloxy-1-(triphenyl-λ⁵-phosphanylidene)-nona-6,8-dien-2-one 
• 193553-76-3 2,3,4-tri-O-benzyl-5,6,7,8-tetradeoxy-D-lyxo-octadi-5(E),7-enol 
• 159878-45-2 methyl 4(R),5(S),6(R)-tri-O-benzyl-dec-2(E),7(E),9-trienoate 

Relevant academic research and scientific papers

Stability of regioisomeric sugar allyltins. Cleavage of the carbon-oxygen bond under radical conditions

Secondary sugar allyltin derivatives [Sug-CH(SnBu3)-CH=CH2] decompose at high temperature (140°C) with elimination of the tin moiety and opening of the sugar ring. The cis-dienoaldehydes thus formed react with Ph3P=CH-CO2Me to afford the corresponding trienes, which spontaneously undergo stereoselective intramolecular [4+2] cycloaddition to optically pure, highly oxygenated bicyclo[4.3.0]nonene derivatives. Primary sugar allyltins [Sug-CH=CHCH2-SnBu3] are thermally stable and do not decompose up to 170°C.

FROM SUGAR ALLYLTIN DERIVATIVES TO CHIRAL DIENOALDEHYDES AND TRIENOATES

Sugar dialdoses 5, 9, 15, and 16 were converted into allyltin derivatives 4, 12, 13, and 14, in yields of 35 - 47percent respectively.Treatment of 4, 12, and 13 with a mild Lewis acid (ZnCl2) in methylene chloride caused rearrangement to appropriate dieno