189177-99-9

Upstream product

• 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 
• 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 

Downstream Products

• 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 

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.