220094-57-5

Upstream product

• 162189-53-9 (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane 
• 162189-52-8 {(S)-3-[(4S,5R,6R)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-3-methoxy-prop-1-ynyl}-tert-butyl-dimethyl-silane 
• 162189-51-7 tert-Butyl-{(S)-3-methoxy-3-[(4S,5R,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-phenylsulfanyl-ethyl)-[1,3]dioxan-4-yl]-prop-1-ynyl}-dimethyl-silane 
• 162189-50-6 (R)-2-{(4R,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propionaldehyde 
• 220094-53-1 (S)-2-{(4S,5R,6S)-6-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-propan-1-ol 
• 541-41-3 chloroformic acid ethyl ester 
• 220094-56-4 tert-Butyl-{(E)-(1S,6S,7R,10S)-6,7-dimethoxy-10-[(4S,5R,6S)-6-((S)-1-methoxy-prop-2-ynyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-phenyl-undec-8-enyloxy}-dimethyl-silane 

Downstream Products

• 162189-64-2 (E)-(1R,5S,10S,11R,14S,15S,16S,17S,18R)-1,17-Dihydroxy-10,11,18-trimethoxy-14,16-dimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one 
• 162189-56-2 [(2R,3R,4S,5S,6S)-2,4-Dihydroxy-6-((E)-(1S,4R,5S,10S)-10-hydroxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-3-methoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid ethyl ester 
• 162189-61-9 [(2R,3R,4S,5R,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-((E)-(1S,4R,5S,10S)-10-hydroxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-2,3-dimethoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid 
• 220094-61-1 (E)-(1R,5S,10S,11R,14S,15S,16R,17S,18R)-17-(tert-Butyl-diphenyl-silanyloxy)-1,10,11,18-tetramethoxy-14,16-dimethyl-5-phenyl-4,19-dioxa-bicyclo[13.3.1]nonadec-12-en-3-one 
• 220094-59-7 Thexyldimethylsilyl 5-O-(tert-butyldiphenylsilyl)-2-desmethyl-17-hydroxy-3-O-methyl-1,17-secosoraphenic ester 
• 220094-58-6 [(2R,3R,4S,5R,6S)-6-((E)-(1S,4R,5S,10S)-10-Acetoxy-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl)-4-(tert-butyl-diphenyl-silanyloxy)-2,3-dimethoxy-5-methyl-tetrahydro-pyran-2-yl]-acetic acid 2-trimethylsilanyl-ethyl ester 

Relevant academic research and scientific papers

Total synthesis of soraphen A(1α)

The convergent synthesis of macrolide soraphen A(1α) is described starting from glucose (western part) and mannose (eastern part). Mannose was converted into a 2-deoxyribohexopyranoside that could be methylated and reduced stereoselectively. Chain elongation at C-6 was carried out by stereoselective addition of a magnesium acctylide. The two fragments (western and eastern) were assembled by a Julia olefination followed by macrolactonization. The introduction of the methyl group at C-2 of norsoraphen occurred stereoselectively for thermodynamic reasons.