TY - JOUR
T1 - Synthesis of pseudo-trehaloses
T2 - [(1,2, 4 3,5)-2,3,4-trihydroxy-5-hydroxymethyl-1-cyclohexyl] d-glucopyranosides
AU - Ogawa, Seiichiro
AU - Yokoi, Shigeki
AU - Kimura, Noritaka
AU - Shibata, Yasushi
AU - Chida, Noritaka
N1 - Funding Information:
We thank Messrs. Akio Takahashi and Hisao Arita for elemental analyses, Professor Klaus Bock (The Technical University of Denmark) for helpful discussion, and Dr. Nobuo Ohno (Sumitomo Chemical Co. Ltd., Takarazuka) for carrying out the bioassays. The work was supported, in part, by a grant from the Asahi Glass Foundation for the contribution to industrial technology.
PY - 1988/10/1
Y1 - 1988/10/1
N2 - All the theoretically possible, foru diastereoisomeric pairs, α,α (2A and 2B), α,β (3A and 3B), β,α (4A and 4B), and β,β (5A and 5B), of pseudo-trehalose, composed of d-glucopyranose and pseudo-d- or l-glucopyranose, have been synthesised by coupling of the appropriately protected pseudo-α- (6) and -β-dl-glucopyranoses (9) with d-glucopyranose derivatives (10 and 11) in the presence of trimethylsilyl trifluoromethanesulfonate. Elucidation of the structures and absolute configurations of the pseudo-disaccharides was based on the 1H-n.m.r. spectra of their octa-acetates and the optical rotations. None of the pseudo-trehaloses inhibited trehalase.
AB - All the theoretically possible, foru diastereoisomeric pairs, α,α (2A and 2B), α,β (3A and 3B), β,α (4A and 4B), and β,β (5A and 5B), of pseudo-trehalose, composed of d-glucopyranose and pseudo-d- or l-glucopyranose, have been synthesised by coupling of the appropriately protected pseudo-α- (6) and -β-dl-glucopyranoses (9) with d-glucopyranose derivatives (10 and 11) in the presence of trimethylsilyl trifluoromethanesulfonate. Elucidation of the structures and absolute configurations of the pseudo-disaccharides was based on the 1H-n.m.r. spectra of their octa-acetates and the optical rotations. None of the pseudo-trehaloses inhibited trehalase.
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U2 - 10.1016/0008-6215(88)84022-9
DO - 10.1016/0008-6215(88)84022-9
M3 - Article
AN - SCOPUS:0007363513
SN - 0008-6215
VL - 181
SP - 57
EP - 66
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -