Regioselective synthesis of 1I,1II,5I,5II,6I,6I,6II,6II-2H8-cellobiose.
Partially deuteriated 1,5,6,6-(2)H(4)-d-glucose and 1(I),1(II),5(I),5(II),6(I),6(I),6(II),6(II)-(2)H(8)-d-cellobiose were synthesized in high yields and on a large scale from d-glucose. (2)H enrichment at C-5 and C-6 of each glucopyranosyl unit in excess of 85% and 90%, respectively, was realized by (1)H-(2)H exchange in (2)H(2)O containing deuteriated Raney Ni. Nucleophilic addition of LiAlD(4) to 5,6,6-(2)H(3)-2,3,4,6-tetra-O-benzyl-d-gluconolactone led to a 98% (2)H enrichment at C-1. Deuteriated cellobiose is of interest as building block for the synthesis of a model compound of cellulose I.
Zhang
Fuyi
F
Laboratorium für Organische Chemie, ETH Zürich, Switzerland.
Vasella
Andrea
A
D000081:Acetamides; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002475:Cellobiose / Q000138:chemical synthesis* / Q000737:chemistry*; D062845:Chloroacetates; D002855:Chromatography, Thin Layer / Q000379:methods; D003903:Deuterium / Q000737:chemistry; D005942:Gluconates / Q000737:chemistry; D005947:Glucose / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007783:Lactones; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D011714:Pyrans / Q000737:chemistry; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry; D014867:Water / Q000737:chemistry