The synthesis of the 2- and 2′-monodeoxygenated analogues of β-maltosyl-(1→4)-trehalose

Article abstract of DOI:10.1080/07328309808002338

Two derivatives of β-maltosyl-(1→4)-trehalose monodeoxygenated at C-2 or C-2′ have been synthesized in [2+2] block syntheses. N-Iodosuccinimide-mediated coupling of tetra-O-benzyl-glucose to tri-O-acetyl-D-glucal followed by O-acetylation furnished 3,4,6-tri-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (7), which was used as a starting material for both tetrasaccharides. For the preparation of the 2′-monodeoxygenated saccharide the deoxyiodo pyranose moiety of 7 was further elaborated by de-O-acetylation, O-benzylidenation, O-benzylation, and selective reductive opening of the benzylidene acetal to give glycosyl acceptor 10. Glycosylation with hepta-O-acetylmaltosyl bromide and deprotection including removal of the iodo substituent afforded the 2′-deoxymaltosyl-(1→4)-trehalose 14. On the other hand, the non-iodinated pyranose moiety of 7 was transformed to a glycosyl acceptor. The removal of the benzyl groups of 7 necessitated also the reduction of the iodo group at this early stage. The resulting 3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl α-D-glucopyranoside was subjected to a similar reaction sequence as above to finally result in the 2-deoxymaltosyl-(1→4)-trehalose 22.

Full text of DOI:10.1080/07328309808002338

Journal of Carbohydrate Chemistry
ISSN: 0732-8303 (Print) 1532-2327 (Online) Journal homepage: http://www.tandfonline.com/loi/lcar20
The Synthesis of the 2- and 2′-Monodeoxygenated
Analogues of β-Maltosyl-(1→4)-Trehalose
Hans Peter Wessel & Rudolf Minder
To cite this article: Hans Peter Wessel & Rudolf Minder (1998) The Synthesis of the 2- and
2′-Monodeoxygenated Analogues of β-Maltosyl-(1→4)-Trehalose , Journal of Carbohydrate
Chemistry, 17:4-5, 567-586
To link to this article: http://dx.doi.org/10.1080/07328309808002338
Published online: 22 Aug 2006.
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Date: 07 June 2016, At: 17:33