170708-57-3

Upstream product

• 189177-83-1 C₅₉H₉₈O₉S₅Si 
• 168334-04-1 (S)-5-[(2S,3R,6R,8R,9S)-8-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-3,9-dimethyl-1,7-dioxa-spiro[5.5]undec-2-yl]-3-methyl-pentan-2-one 
• 170708-56-2 <2S,2(3S),3R,6R,8R,8(1S),9S>-3,9-dimethyl-2-<3-(2-methyl-1,3-dithian-2-yl)butyl>-8-<1-methyl-2-(phenylsulfonyl)ethyl>-1,7-dioxaspiro<5,5>undecane 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 189177-84-2 (2S,3S,6R)-2-{2-[(2R,3R,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-(4-methoxy-benzyloxy)-5-methyl-hexyl]-[1,3]dithian-2-yl}-6-{(2S,3S,6R,8S,9R)-3,9-dimethyl-8-[(S)-3-(2-methyl-[1,3]dithian-2-yl)-butyl]-1,7-dioxa-spiro[5.5]undec-2-yl}-heptan-3-ol 
• 104410-90-4 tert-butyldimethylsilyl trifluoroacetate 
• 170708-51-7 (2R,3S,6R,7S,8R)-6-(t-butyldimethylsiloxy)-1,2-epoxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 

Downstream Products

• 109946-35-2 tautomycin 

Relevant academic research and scientific papers

Total synthesis of (+)-tautomycin

The synthesis of Segment B/C corresponding to the C26 through to the C1 positions of tautomycin was achieved by coupling between Segment B (an epoxide) and Segment C (a sulfone carbanion) in the presence of baron trifluoride etherate (BF3·OEt2). Two routes have been developed in esterification of Segment A with Segment BIG. The first route employed Segment A with furan moiety as masked maleic anhydride, In the second route, maleic anhydride as Segment A was directly used to accomplish the improved synthesis. Removal of the silyl protecting group with pyridinium poly(hydrogen fluoride) (HF-Py) at the final step completed the total synthesis of tautomycin.

Total synthesis of (+)-tautomycin

Tautomycin molecule was disconnected into 3 retrosynthetic segments, A, B, and C, each of which was synthesized in optically active form. First coupling between Segments B and C was achieved between an epoxide and a sulfone carbanion in the presence of BF