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Synthesis of Conandroside: A Dihydroxyphenylethyl Glycoside from Conandron ramaidioides
Author(s) -
Kawada Toshinari,
Asano Ryuji,
Makino Kozo,
Sakuno Tomoyasu
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200008)2000:15<2723::aid-ejoc2723>3.0.co;2-y
Subject(s) - chemistry , methylamine , derivative (finance) , potassium carbonate , methanol , dimethyl sulfate , medicinal chemistry , glycoside , potassium , organic chemistry , stereochemistry , economics , financial economics
The key intermediate 2‐(3,4‐di‐ O ‐benzylphenyl)ethyl 2,6‐di O ‐acetyl‐4‐ O ‐[( E , Z )‐3,4‐di‐ O ‐benzylcaffeoyl)‐β‐ D ‐glucopyranoside (3) was xylosylated with peracetylated xylosyl trichloroacetimidate donor 4 to afford conandroside derivative 5 . Deacetylation of compound 5 with a methanol solution of methylamine resulted in the formation of compound 6 , the monoacetyl derivative 6a and the caffeoyl‐migrated derivative 6b in yields of 54%, 19% and 15%, respectively. Compound 6 was then debenzylated with 1,4‐cyclohexadiene/palladium−carbon to afford conandroside ( 1 ), which was treated with dimethyl sulfate in the presence of potassium carbonate to produce the methylated conandroside 2 . This compound was found to be identical to the reported “conandroside tetra‐ O ‐methyl ether” obtained by methylation of the extract from Conandron ramoidioides .