177536-82-2

Upstream product

• 177536-80-0 6-O-Acetyl-2-O-(cyclohexylcarbamoyl)-3,4-O-(2,2,2-trichloroethylidene)-α-D-altropyranosyl fluoride 
• 108-98-5 thiophenol 
• 177536-81-1 Acetic acid (2S,3aR,4R,6R,7S,7aR)-7-cyclohexylcarbamoyloxy-6-phenylsulfanyl-2-trichloromethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester 

Relevant academic research and scientific papers

Studies with altrose derivatives - A convenient approach to α-linked digitoxosides

The 2-O-(cyclohexylcarbamoyl)-3,4-O-(2,2,2-trichloroethylidene)-protected α-altropyranosyl fluorides 1, 7, and 11 were used as starting materials for intra- and intermolecular glycosylations in the presence of BF3. Because of the effective neighbouring group participation of the carbamoyl moieties, the corresponding trans-glycosides 2, 4, 6, 12, and 14 can be stereoselectively prepared from 1 and 11, respectively, in good yields. In the case of the 6-O-formyl derivative 7 the intramolecular glycosylation to 1,6-anhydro-2-O-(cyclohexylcarbamoyl)-3,4-O-(2,2,2-trichloroethylidene)-β- D-altropyranoside (8) is possible, when no other competing nucleophiles are present. Furthermore, the deoxygenation of the altrose moiety of 6-O-[6-deoxy-3,4-O-(2,2,2-trichloroethylidene)-α-L-altropyranosyl]-1,2:3, 4-di-O-isopropylidene-α-D-galactopyranose (15) in 2-position and the hydrogenolysis of the trichloroethylidene acetal protecting group were simultaneously realised. 6-O-(2,6-Dideoxy-3,4-O-ethylidene-α-L-ribo-hexopyranosyl)-1,2:3,4-di-O- isopropylidene-α-D-galactopyranose (16) was obtained by reduction of the intermediately prepared 2-xanthate of 15 with Bu3SnH/AIBN. VCH Verlagsgesellschaft mbH, 1996.