114197-93-2

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 53962-63-3 Acetic acid (8R,9S,13S,14S,16S)-16-acetoxymethyl-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl ester 
• 114197-91-0 16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol 
• 64336-08-9 16α-hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-ol 
• 114197-92-1 16α-acetoxymethyl-3-methoxyestra-1,3,5(10)-trien-17β-yl p-toluenesulfonate 

Relevant academic research and scientific papers

Steroids, XXXVIII. Neighbouring Group Participation, IX. Preparation of 16α-Hydroxymethyl-3-methoxyestra-1,3,5(10)-trien-17α-ol and Solvolysis Investigations

Solvolysis of the p-toluenesulfonate 1d in acetic acid and in dimethyl sulfoxide yields 5b with inversion at C-17.The conversion can be explained by a neighbouring group participation characterized by the general symbol (AcO-6).In order to confirm the participation of the 16α-acetoxymethyl group in 1d, comparative solvolytic investigations were carried out with the toluenesulfonate 9.