170708-56-2

Upstream product

• 109-80-8 1.3-propanedithiol 
• 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 

Downstream Products

• 170708-57-3 C₅₉H₁₀₈O₇S₄Si₂ 
• 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 
• 189178-01-6 (2S,3S,6R)-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}-2-{2-[(4R,5S,6R)-6-isopropyl-5-methoxy-2-(4-methoxy-phenyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dithian-2-yl}-heptan-3-ol 
• 109946-35-2 tautomycin 
• 189178-00-5 C₅₃H₈₂O₉S₅ 
• 189177-83-1 C₅₉H₉₈O₉S₅Si 

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.