150422-81-4

Upstream product

• 70-55-3 toluene-4-sulfonamide 
• 135456-80-3 (Z)-(2R,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-enal 
• 4104-47-6 N-sulfinyl-p-toluenesulfonamide 
• 135456-77-8 (3S,4R,5S)-6-(tert-Butyl-dimethyl-silanyloxy)-3,4,5-trimethoxy-1-trimethylsilanyl-hex-1-yne 
• 135456-76-7 tert-Butyl-((2S,3R,4S)-6,6-dibromo-2,3,4-trimethoxy-hex-5-enyloxy)-dimethyl-silane 
• 135456-74-5 ((2S,3S,4R)-5,5-Bis-ethylsulfanyl-2,3,4-trimethoxy-pentyloxy)-tert-butyl-dimethyl-silane 
• 135456-75-6 (2R,3S,4S)-5-(tert-Butyl-dimethyl-silanyloxy)-2,3,4-trimethoxy-pentanal 
• 135456-79-0 (Z)-(2S,3R,4S)-2,3,4-Trimethoxy-6-trimethylsilanyl-hex-5-en-1-ol 
• 135456-73-4 O²,O³,O⁴-trimethyl-L-arabinose diethyl dithioacetal 

Downstream Products

• 150422-83-6 N-(6-Iodo-benzo[1,3]dioxole-5-carbonyl)-4-methyl-N-((1R,4S,5R,6S)-4,5,6-trimethoxy-cyclohex-2-enyl)-benzenesulfonamide 

Relevant academic research and scientific papers

An Approach to Total Synthesis of (+)-Lycoricidine

A convergent synthesis of a protected version of (+)-lycoricidine has been accomplished in 13 steps from L-arabinose.Preparation of the aminocyclitol moiety 50 employed a novel vinylsilane-terminated N-sulfonyliminium ion cyclization of vinylsilane aldehyde 42.Closure of the B-ring using an intramolecular Heck reaction afforded lycoricidine derivative 58.An unexpected cyclization of vinylsilane aldehyde 42 allowed for the stereodivergent preparation of semiprotected conduritols 43 and 45.

SYNTHETIC APPLICATIONS OF N-SULFONYL IMINES

N-Tosyl imines, prepared from aldehydes and N-sulfinyl-p-toluene sulfonamide (Kresze reaction), cyclize with alkenes and vinyl silanes in the presence of a Lewis acid to afford intermediates useful for alkaloid total synthesis.