207226-46-8

Upstream product

• 207226-43-5 (E)-(4R,5R,6S)-7-Benzyloxy-4,6-dimethyl-hept-2-ene-1,5-diol 
• 140925-54-8 (2R,3R,4R,5S,6S)-7-Benzyloxy-2,4,6-trimethyl-heptane-1,3,5-triol 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 207226-47-9 (R)-2-{(4R,5R,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde 
• 207226-48-0 (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol 
• 114597-34-1 (2S,3R)-3-benzyloxymethoxy-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentane 
• 207461-75-4 (S)-2-{(4S,5S,6R)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol 

Relevant academic research and scientific papers

Synthesis of Stereopentad Subunits of Zincophorin and Rifamycin-S through Use of Chiral Allenyltin Reagents

The anti,anti adduct 3, from addition of the allenic stannane (P)-2 to the a-methyl-β-OBn aldehyde (S)-1 promoted by SnCl4, was converted to the stereopentad 6 by a sequence involving reduction to the (E)-allylic alcohol with Red-Al, Sharpless asymmetric epoxidation, and addition of the higherorder methyl cyanocuprate to the derived epoxide 5. Stereopentad 6 was converted to the acetonide acetal 15, an intermediate in Danishefsky's synthesis of zincophorin. By a similar sequence, adduct ent-4 was converted, via diol 19, to stereopentad 22, an intermediate in Kishi's synthesis of rifamycin-S. An alternative route to diol 19 was achieved from the MOM-protected derivative 28 of epoxy diol 18.