The utility of a 3-O-allyl group as a protective group for ring-opening polymerization of alpha-D-glucopyranose 1,2,4-orthopivalate derivatives.
To clarify the utility as a protective group of 3-O-allyl group on ring-opening polymerization of alpha-D-glucopyranose 1,2,4-orthopivalate derivatives, four orthopivalate derivatives, 3-O-allyl-6-O-pivaloyl- (1), 3-O-allyl-6-O-benzyl- (2), 3,6-di-O-allyl- (3), and 3-O-allyl-6-O-methyl-alpha-D-glucopyranose 1,2,4-orthopivalates (4), were selected as starting monomers and were polymerized under -30 degrees C in CH2Cl2 using BF3.Et2O as a catalyst. All the orthopivalate derivatives 1-4 were found to give stereoregular polysaccharides, (1-->4)-beta-D-glucopyranans. Thus, it was concluded that the allyl group as a protective group at 3-O position of glucose othropivalate is acceptable to yield stereoregular (1-->4)-beta-D-glucopyranans, cellulose derivatives.
Karakawa
Makoto
M
Division of Forest and Biomaterials Science, Graduate School of Agriculture, Kyoto University, Sakyo-Ku, Kyoto 606-8502, Japan. karakawa@kais.kyoto-u.ac.jp
Kamitakahara
Hiroshi
H
Takano
Toshiyuki
T
Nakatsubo
Fumiaki
F
D000498:Allyl Compounds / Q000737:chemistry; D002482:Cellulose / Q000138:chemical synthesis*; D005947:Glucose / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D014631:Valerates / Q000737:chemistry
D000498:Allyl Compounds; D014631:Valerates; D002482:Cellulose; D005947:Glucose