学位論文

糖を側鎖に持つAzulene誘導体の合成

SYNTHESIS OF AZULENE DERIVATIVES WITH A SIDE CHAIN

jpn

2007-03-24

Not Applicable (or Unknown)

2007-03-24

修士(工学)

工学研究科物質化学専攻; 指導教授: 中村暢男

Introduction of sugar side chains to azulene derivatives would raise physiological activities of azulenes. Thus, synthetic approaches to these derivatives were explored. Reaction of 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide(TAGB) with azulene carboxylic acids derived from 3-formylguaiazulene by modified Reformatsky or aldol condensation reactions at room temperature afforded the corresponding azulene glycosyl esters in good yields. Deprotection of the 6-O-trityl group of 1,2,3,4-O-tetraacetyl-6-O-triphenymethylglucose under acidic conditions was not achieved. Esterification of the azulene carboxylic acids under Mitsunobu reaction conditions, and condensation of a glucosamine with 3-socyanoguaiazulene by Ugi reaction were also reported.

Thesis