1373934-46-3

Upstream product

• 1373934-43-0 ethyl (2E)-2-{(4S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}acetate 
• 1373934-34-9 (4R,5R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-ol 
• 1373934-33-8 (4R,5R)-5-(benzyloxy)-4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxane 
• 1373934-40-7 (4R,5R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-one 
• 1373934-37-2 (4R,5R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ol 

Downstream Products

• 1373934-73-6 C₂₇H₃₄Cl₃NO₄Si 
• 1219844-09-3 N-{(4S,5R)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-yl}-2,2,2-trichloroacetamide 
• 1373934-70-3 N-{(4S,5S)-4-[(tert-butyldiphenylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-yl}-2,2,2-trichloroacetamide 
• 1373934-49-6 (4S,2E)-tert-butyl{[2,2-dimethyl-5-(2-thiocyanatoethylidene)-1,3-dioxan-4-yl]methoxy}diphenylsilane 
• 1373934-52-1 tert-butyl{[(4S,5R)-5-isothiocyanato-2,2-dimethyl-5-vinyl-1,3-dioxan-4-yl]methoxy}diphenylsilane 
• 1373934-67-8 tert-butyl{[(4S,5S)-5-isothiocyanato-2,2-dimethyl-5-vinyl-1,3-dioxan-4-yl]methoxy}diphenylsilane 

Relevant academic research and scientific papers

An efficient synthesis of the polar part of sulfamisterin and its analogs

An efficient synthesis of the polar part of sulfamisterin and its analogs starting from d-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the substituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs.

Total synthesis of mycestericin A and its 14-epimer

The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species synthesized from d-tartrate under the Negishi or Suzuki-Miyaura coupling conditions, followed by deprotection, completed the total synthesis of 1. The 14-epimer of mycestericin A was also synthesized, and a comparison of [α]D values of peracetyl γ-lactone derivatives of mycestericin A and its 14-epimer as well as degradation studies of 1 and 34 fully confirmed the proposed absolute structure of mycestericin A.