319922-76-4

Upstream product

• 228419-55-4 (Z)-γ-(tert-butyldimethylsilanyloxy)methallyltributylstannane 
• 228419-57-6 (2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-hex-5-en-3-ol 
• 79271-56-0 triethylsilyl trifluoromethyl sulfonate 
• 228419-66-7 (2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-3-triethylsilanyloxy-hex-5-en 
• 160238-46-0 (2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal 

Downstream Products

• 319922-69-5 1-(4-triethylsilanyloxy-5-(4-methoxy-phenoxy)-6-(tert-butyldiphenyl-silanyloxy-ethyl)-tetrahydro-pyran-2-yl)-1-(tert-butyl-dimethyl-silanyloxy)-2-trimethylsilanyloxy-prop-2-ene 
• 319921-83-0 1-(4-triethylsilanyloxy-5-(4-methoxy-phenoxy)-6-(tert-butyldiphenyl-silanyloxy-ethyl)-tetrahydro-pyran-2-yl)-1-(tert-butyl-dimethyl-silanyloxy)-propan-2-one 
• 319922-86-6 3-(tert-butyl-dimethyl-silanyloxy)-3-[4'-triethylsilanyloxy-5'-(4-methoxy-phenoxy)-6'-hydroxyethyl-3'-methyl-tetrahydro-pyran-2'-yl]-2-methyl-1,2-propanediol 
• 319922-88-8 1-(4-triethylsilanyloxy-5-(4-methoxy-phenoxy)-6-(hydroxyethyl)-tetrahydro-pyran-2-yl)-1-(tert-butyl-dimethyl-silanyloxy)-propan-2-one 
• 319922-84-4 (4R,5R,6R,7R,8S,4'S)-8-(tert-butyldimethylsilanyloxy)-5-hydroxy-4-(4-methoxy-phenoxy)-6-methyl-8-(4'-methyl-2-oxo-[1,3]-dioxolan-4-yl)-7-triethylsilanyloxy-oct-2-enoic acid methyl ester 
• 319922-50-4 [6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester 
• 228419-61-2 4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one 
• 228419-64-5 (2S,3R,4R,5R,6S)-6-(tert-butyldimethylsilanyloxy)-2-(4-methoxy-phenoxy)-4-methyl-6-((2S)-4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-5-triethylsilanyloxy-3-hydroxyhexanal 
• 228419-54-3 [6-[1'-(tert-butyl-dimethyl-silanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-hydroxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester 
• 228419-65-6 (4R,5R,6R,7R,8S,4'S)-8-(tert-butyldimethylsilanyloxy)-4-(4-methoxy-phenoxy)-5,7-dihydroxy-6-methyl-8-(4'-methyl-2-oxo-[1,3]-dioxolan-4-yl)-oct-enoic acid methyl ester 
• 319922-82-2 4-[1-(tert-butyldimethylsilanyloxy)-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-4,6,7-triol]-4-methyl-[1,3]-dioxolan-2-one 
• 228419-59-8 4-[(1S,2R,3R)-1-(tert-butyldimethylsilanyloxy)-4-(4-methoxy-benzyloxy)-3-methyl-2-triethylsilanyloxy-butyl]-4-methyl-[1,3]-dioxolan-2-one 

Relevant academic research and scientific papers

Synthesis of the C(29)-C(45) bis-pyran subunit (E-F) of spongistatin 1 (altohyrtin A)

A synthesis of the C(29)-C(45) bis-pyran subunit 2 of spongistatin 1 (1a) is described. The synthesis proceeds in 19 steps from the chiral aldehyde ent-7, and features highly diastereoselective α-alkoxyallylation reactions using the γ-alkoxy substituted allylstannanes 17 and 19, as well as a thermodynamically controlled intramolecular Michael addition to close the F-ring pyran. The E ring was assembled via the Mukaiyama aldol reaction of F-ring methyl ketone 3 and the 2,3-syn aldehyde 4.