189178-01-6

Upstream product

• 189177-98-8 (2R,3S)-3-{2-[(4R,5S,6R)-6-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-butane-1,2-diol 
• 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 
• 189177-99-9 (4R,5S,6R)-4-Isopropyl-5-methoxy-2-(4-methoxy-phenyl)-6-[2-((S)-(R)-1-oxiranyl-ethyl)-[1,3]dithian-2-ylmethyl]-[1,3]dioxane 
• 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 
• 170708-54-0 (2R,3S,6R,7S,8R)-6-hydroxy-1,2-isopropylidenedioxy-7-methoxy-8-(4-methoxybenzyl)oxy-3,9-dimethyl-4-(1,3-dithian-2-yl)-decane 
• 189178-00-5 C₅₃H₈₂O₉S₅ 

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.