209113-75-7Relevant academic research and scientific papers
An expeditious route to the synthesis of kelampayosides A and B
Duynstee, Howard I.,De Koning, Martijn C.,Van der Marel, Gijs A.,Van Boom, Jacques H.
, p. 9881 - 9898 (1999)
Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri- O-benzoyl-1-thio-β-D-glucopyranoside (13) with ethyl 2,3-di-O-acetyl-5-O- benzyl-1-thio-α/β-erythro-apiofuranoside (4a) gave direct 14 in an excellent yield. BF3·Et2O-catalysed condensation of the α- trichloroacetimidate 31, accessible in two steps from 14, with 3,4,5- trimethoxyphenol gave β-linked derivative 32 followed by deprotection gave Kelampayoside A. Protecting group manipulations of 32 and subsequent caffeoylation of resulting 36 followed by deprotection gave Kelampayoside B.
Synthesis of 3,4,5-trimethoxyphenyl 5-O-caffeoyl-β-D-erythro- apiofuranosyl-(1→6)-β D-glucopyranoside: Kelampayoside B
Duynstee, Howard I.,De Koning, Martijn C.,Van Der Marel, Gijs A.,Van Boom, Jacques H.
, p. 4129 - 4132 (2007/10/03)
Chemoselective NIS/cat. TfOH-mediated glycosylation of ethyl 2,3,4-tri- O-benzoyl-1-thio-β-D-glucopyranoside (4) with ethyl 2,3-di-O-acetyl-5-O- benzyl-1-thio-β-D-erythro-apiofuranoside (3) gave dimer 5 in an excellent yield. BF3Et2O-catalysed condensation of the α-trichloroacetimidate 18, accessible in two steps from 5, with 3,4,5-trimethoxyphenol gave β-linked derivative 19 which could be transformed in five steps into the title compound.
