127492-48-2

Upstream product

• 127492-45-9 <2S-<2α,4α,5α,6α>>-(1,1-Dimethylethyl)<<4-<2-<6-ethenyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl>-1-propenyl>-2-methoxycyclohexyl>oxy>dimethylsilane 
• 118207-43-5 (1R,2R,4R)-2-methoxy-4-<(phenylsulfonyl)methyl>-1-<<(1,1-dimethylethyl)dimethylsilyl>oxy>cyclohexane 
• 127308-74-1 (2S,4S,5R,6R)-2-(4-methoxyphenyl)-5-methyl-6-vinyl-1,3-dioxane-4-carboxaldehyde 
• 127492-41-5 2-Benzenesulfonyl-2-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-[(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-5-methyl-6-vinyl-[1,3]dioxan-4-yl]-ethanol 
• 127492-42-6 2-Benzenesulfonyl-2-[(1R,3R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-1-[(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-5-methyl-6-vinyl-[1,3]dioxan-4-yl]-ethanone 
• 127492-43-7 <2S-<2α,4α(1S*,3S*,4S*),5α,6α>>2-<4-<<(1,1-Dimethylethyl)dimethylsilyl>oxy>-3-methoxycyclohexyl>-1-<6-ethenyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl>ethanone 
• 127492-44-8 1-[(1R,3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-cyclohexyl]-2-[(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-5-methyl-6-vinyl-[1,3]dioxan-4-yl]-propan-2-ol 
• 127492-46-0 (1R,2R,4R)-2-Methoxy-4-{(E)-2-[(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-5-methyl-6-vinyl-[1,3]dioxan-4-yl]-propenyl}-cyclohexanol 
• 171011-79-3 (E,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-heptan-2-ynyl 1,1,1-trimethylacetate 
• 171011-81-7 (2E,2R,3R,4S,5S)-4,6-Dimethyl-2,3-epoxy-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2,6-heptadien-1-ol 
• 171011-80-6 (2E,4R,5S,6E)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-2,6-heptadien-1-ol 
• 89238-99-3 O-(4-methoxybenzyl)-trichloroacetimidate 
• 171011-82-8 (E,3S,4R,5S)-4,6-Dimethyl-5-<(p-methoxybenzyl)oxy>-7-<(1R,3R,4R)-3-methoxy-4-<(triisopropylsilyl)oxy>cyclohexyl>-6-hepten-1,3-diol 
• 127492-47-1 <2S-<2α,4α,5α,6α>>-<<4-<2-<6-ethenyl-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl>-1-propenyl>-2-methoxycyclohexyl>oxy>tris-(1-methylethyl)silane 

Downstream Products

• 127492-54-0 C₇₄H₁₃₀O₁₂S₃Si₃ 
• 127492-51-7 C₅₀H₈₅NO₉Si₂ 
• 127492-52-8 (S)-2-((R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-{(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-6-[(E)-2-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-5-methyl-[1,3]dioxan-4-yl}-ethyl)-pent-4-enoic acid benzyl ester 
• 127492-50-6 (S)-3-[(S)-2-((R)-1-Hydroxy-2-{(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-6-[(E)-2-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-5-methyl-[1,3]dioxan-4-yl}-ethyl)-pent-4-enoyl]-4-isopropyl-oxazolidin-2-one 
• 127516-99-8 (S)-2-((R)-1-(tert-Butyl-dimethyl-silanyloxy)-2-{(2S,4S,5R,6S)-2-(4-methoxy-phenyl)-6-[(E)-2-((1R,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-1-methyl-vinyl]-5-methyl-[1,3]dioxan-4-yl}-ethyl)-pent-4-enal 
• 127492-49-3 <2S-<2α,4α,5α,6α>>-2-(4-Methoxyphenyl)-6-<2-<3-methoxy-4-<oxy>cyclohexyl>-1-methylethenyl>-5-methyl-1,3-dioxane-4-acetaldehyde 

Relevant academic research and scientific papers

Synthesis of a C22-34 subunit of the immunosuppressant FK-506

A new route to the C22-34 subunit of FK-506 was developed. A highly diastereoselective Diels-Alder reaction of 1,3-butadiene with the bis-acrylate of (R,R)-hydrobenzoin and subsequent saponification provided the cyclohexenecarboxylic acid 6.4 of 95% ee. Elaboration to the enal 9.2 was effected by known transformations. Enal 9.2 underwent diastereoselective and enantiospecific S(E)2' addition of allenyl stannane (S)-3.9 affording the homopropargylic alcohol 9.3 as an 85:15 syn/anti mixture. The PMB ether 9.5 was converted to the known benzylidene derivative 10.4 by sequential treatment with Red-Al, epoxidation, a second reduction with Red-Al, and oxidative benzylidene formation with DDQ.

A Formal Synthesis of FK-506. Exploration of Some Alternatives to Macrolactamization

The coupling of the previously described subunits 2, 3, and 4 is described.The C28-C27 E-double bond is fashioned from a sulfurane induced dehydration of alcohol 11.The C19-C20 E-double bond was constructed via a modified Julia process culminating in a reductive elimination of a vicinal trifluoroacetoxy sulfone (see 22 -> 23 -> 24 and 25).The synthesis of intermediates anticipating potential macrolactonization are also described.