181208-08-2

Upstream product

• 181208-05-9 (2R,3S)-2-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran 

Downstream Products

• 196795-17-2 (4aS,6R,9aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-hexahydro-1,5-dioxa-benzocyclohepten-7-one 
• 181208-35-5 (2R,3S,4aR,8aR,9aS,10aS)-2-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-(tert-butyl-dimethyl-silanyloxy)-decahydro-1,8,10-trioxa-anthracene 
• 181208-20-8 (2R,3S,4aR,8aS)-2-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-3-(tert-butyl-dimethyl-silanyloxy)-octahydro-pyrano[3,2-b]pyran 
• 181208-38-8 (2R,4aR,5aS,6aR,10aS,11aR,12aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-dodecahydro-1,5,7,11-tetraoxa-naphthacen-3-one 
• 181208-23-1 (2R,4aR,8aR,9aS,10aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-octahydro-1,8,10-trioxa-anthracen-3-one 
• 181208-26-4 (2R,3S,4aR,8aR,9aS,10aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-decahydro-1,8,10-trioxa-anthracen-3-ol 
• 196795-22-9 (4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-7-triethylsilanyloxy-octahydro-1,5-dioxa-benzocycloheptene 
• 196795-34-3 (4aS,6R,7S,9aR)-6-[(2R,3S)-2-Benzenesulfonyl-3-(tert-butyl-diphenyl-silanyloxymethyl)-oxiranylmethyl]-octahydro-1,5-dioxa-benzocyclohepten-7-ol 
• 196795-26-3 (4aS,5aR,9R,10aS,12aR)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-decahydro-1,5,10-trioxa-benzo[b]heptalen-8-one 
• 196795-23-0 (2R,4aR,5aS,9aR,11aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-decahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-one 
• 196795-24-1 (2R,3S,4aR,5aS,9aR,11aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-dodecahydro-1,5,9-trioxa-dibenzo[a,d]cyclohepten-3-ol 
• 181208-11-7 (2R,3S,4aR,8aS)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-octahydro-pyrano[3,2-b]pyran-3-ol 
• 254442-46-1 (4aS,6R,7S,9aR)-6-[(2R,3S)-3-(tert-butyldiphenylsilyloxymethyl)-3-methyl-2-(toluene-4-sulfonyl)oxiran-2-ylmethyl]-7-methyl-7-(trimethylsilyloxy)octahydro-1,5-dioxabenzocycloheptene 

Relevant academic research and scientific papers

Synthesis of trans-fused polycyclic ethers with angular methyl groups using sulfonyl-stabilized oxiranyl anions

An efficient method has been developed for the synthesis of trans-fused tetrahydropyrans with angular methyl groups adjacent to the ring oxygen. The procedure involves the coupling reaction of a sulfonyl-stabilized oxiranyl anion with an appropriate triflate followed by 6-endo cyclization, and is effective for the construction of 6/6- and 6/7/6-cyclic ether ring systems with sterically congested 1,3-diaxial methyl groups.

Synthesis of methyl-substituted trans-fused tetrahydropyrans via 6-endo cyclization

A stereocontrolled synthesis of methyl-substituted trans-fused tetrahydropyrans having methyl groups adjacent to the ring oxygen is described. The strategy involves the coupling reaction of sulfonyl-stabilized oxiranyl anions with triflates and 6-endo cyc

Stereoselective synthesis of the 6,7,6- and 6,7,7-ring systems of polycyclic ethers by 6-endo cyclization and ring expansion

A new strategy for the stereoselective synthesis of the trans-fused seven-membered cyclic ethers corresponding to subunits of brevetoxin B and hemibrevetoxin B has been developed. The strategy involves alkylation of an oxiranyl anion and B-endo cyclization followed by one-carbon homologation of a tetrahydropyran to an oxepane using trimethylsilyldiazomethane.