585535-20-2

Upstream product

• 585535-19-9 (R)-1-Benzyloxy-3-(2-{(R)-1-[(R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-allyl}-[1,3]dithian-2-yl)-propan-2-ol 
• 121521-25-3 (-)-(2S,3S)-2,3-epoxypent-4-en-1-ol 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 365562-69-2 (-)-tert-butyldimethyl(((2S,3S)-3-vinyloxiran-2-yl-)methoxy)silane 
• 585535-18-8 2-{(R)-1-[(R)-1,2-Bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-allyl}-[1,3]dithiane 

Downstream Products

• 1178869-77-6 C₂₈H₅₂O₅Si₂ 
• 585535-21-3 (4R,6S)-4-Benzyloxymethyl-6-{(S)-1-[(R)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-allyl}-2,2-dimethyl-[1,3]dioxane 
• 585535-22-4 (2R,3R)-3-((4S,6R)-6-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxan-4-yl)-pent-4-ene-1,2-diol 
• 585535-23-5 (4R,6S)-4-Benzyloxymethyl-2,2-dimethyl-6-((S)-(R)-1-oxiranyl-allyl)-[1,3]dioxane 

Relevant academic research and scientific papers

(+)-Rimocidin synthetic studies: Construction of the C(1-27) aglycone skeleton

(Chemical Equation Presented) Assembly of the C(1-27) macrocyclic skeleton of rimocidinolide, the aglycone of (+)-rimocidin (1), has been achieved in convergent fashion. Key features of the synthetic strategy entail application of multicomponent Type I Anion Relay Chemistry (ARC), in conjunction with the SN2/SN2′ reaction manifolds of vinyl epoxides, both employing 2-substituted 1,3-dithianes to construct the C(1-19) carbon backbone. Yamaguchi union of a C(20-27) vinyl borate ester, possessing the all-trans triene, with an advanced C(1-19) vinyl iodide followed by macrocyclization via Suzuki-Miyaura crosscoupling completed construction of the C(1-27) rimocidinolide skeleton.

(+)-Rimocidin synthetic studies. Construction of an advanced C(1-18) polyol fragment

(Matrix presented) The synthesis of an appropriately functionalized advanced C(1-18) polyol fragment of the mycosamine-glycosylated polyene macrolide, (+)-rimocidin (1), has been achieved in a highly efficient manner. Highlights of the strategy include th