A short route to malto-trisaccharide synthons: Synthesis of the branched nonasaccharide, 6 '''-alpha-maltotriosyl-maltohexaose

• Published in: Synthesis (Stuttgart) no. 3; pp. 418 - 426
• Main Authors: Damager, Olsen, CE, Moller, BL, Motawia, MS
• Format: Journal Article
• Language: English
• Published: STUTTGART Thieme Medical Publishers 2002
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; carbohydrates; ONE-POT PREPARATION; phase transfer catalysis; 6'''-alpha-maltotriosyl-maltohexaose; BENZYLIDENE ACETALS; 1,3-berizodithiolan-2-ylium protecting group; SUGARS; DERIVATIVES; glycosides; CHEMICAL SYNTHESIS
• ISSN: 0039-7881
• DOI: 10.1055/s-2002-20038

A short route to phenyl 1-thio-beta-maltotrioside derived building blocks and their use for the synthesis of the branched nonasaccharide. 6"'-alpha-maltotriosyl-maltohexaose, is described. Instead of using glucose and maltose as starting materials, maltotriose was used and synthetically manipulated in a well designed strategy to obtain phenyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-O-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-2,3-di-O-benzyl-1-thio-beta-D-glucopyranoside, phenyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-O-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside and phenyl O-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)(1-->4)-O-(2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside. The described methodology has shortened multi-step synthesis of the desired branched nonasaccharide from 40 to 23 steps. It has also provided maltotriose derived building blocks that independently or in combination with corresponding glucose or maltose derived building blocks permit synthesis of any desired part of the amylopectin or amylose molecule.