2,3,4,6-Tetra-O-benzoyl-D-glucopyranose - CAS 64768-20-3
Product Name:
D-Glucopyranose 2,3,4,6-tetrabenzoate
CAS Number:
Molecular Weight:
Molecular Formula:
Chemical Structure
CAS 64768-20-3 2,3,4,6-Tetra-O-benzoyl-D-glucopyranose

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Reference Reading

1.Synthesis of 4'-O-acetyl-maltose and alpha-D-galactopyranosyl-(1-->4)-D-glucopyranose for biochemical studies of amylose biosynthesis.
Motawia MS1, Olsen CE, Denyer K, Smith AM, Møller BL. Carbohydr Res. 2001 Feb 15;330(3):309-18.
The chemical synthesis of the title compounds as maltose analogs, in which the non-reducing end is modified by acetylation of the 4'-OH group or by reversing its configuration, is reported. For synthesis of the 4'-O-acetylated analog, beta-maltose was converted into its per-O-benzylated-4',6'-O-benzylidene derivative followed by removal of the benzylidene acetal function and selective silylation at C-6'. Acetylation at C-4' of the obtained silylated compound followed by removal of the benzyl ether protecting groups and subsequent desilylation afforded the desired analog. The other maltose analog was synthesized via the glycosidation reaction between the glycosyl donor, O-(2,3,4,6-tetra-O-benzyl-alpha/beta-D-galactopyranosyl)trichloroacetimidate and the glycosyl acceptor, phenyl 2,3,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside followed by removal of the phenylthio group and debenzylation to provide the desired analog.
2.Biosynthetic studies on the alpha-glucosidase inhibitor acarbose: the chemical synthesis of isotopically labeled 2-epi-5-epi-valiolone analogs.
Arakawa K1, Bowers SG, Michels B, Trin V, Mahmud T. Carbohydr Res. 2003 Sep 26;338(20):2075-82.
2-epi-5-epi-valiolone is a cyclization product of the C(7) sugar phosphate, sedoheptulose 7-phosphate, involved in the biosynthesis of the aminocyclitol moieties of acarbose, validamycin, and pyralomicin. As part of our investigation into the pathway from 2-epi-5-epi-valiolone to the valienamine moiety of acarbose, we prepared 1-epi-5-epi-(6-(2)H(2))valiolol [(6-(2)H(2))-6], 5-epi-(6-(2)H(2))valiolol [(6-(2)H(2))-17], 1-epi-2-epi-5-epi-(6-(2)H(2))valiolol [(6-(2)H(2))-12] and 2-epi-5-epi-(6-(2)H(2))valiolamine [(6-(2)H(2))-11]. Compounds (6-(2)H(2))-6 and (6-(2)H(2))-17 were synthesized from 2,3,4,6-tetra-O-benzyl-D-glucopyranose in 10 and seven steps, respectively, whereas (6-(2)H(2))-12 and (6-(2)H(2))-11 were synthesized from 2,3,4,6-tetra-O-benzyl-D-mannopyranose in eight and 10 steps, respectively.