Article

Synthesis and Crystal Structure of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose

Journal of Chemical Crystallography (impact factor: 0.57). 05/2012; 40(1):1-3. DOI:10.1007/s10870-009-9594-0 pp.1-3

ABSTRACT AbstractThe crystal of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose (I) was studied by X-ray diffraction. (I) crystallizes in the monoclinic space group P2

1
with cell parameters of a=5.691(3) Å, b=7.770(2) Å, c=22.503(7) Å, b=93.58(5)°, V=993.1(7) Å3 and Z=2. The molecular structure of (I) consists of a 4,6-O-benzylidene-glucopyranose moiety which has the 4-OH and 6-OH groups of the glucopyranose protected by glycosidic bonding to
a benzylic carbon, forming a benzyl acetal. The other OH groups of the glucopyranose ring are also protected with three acetate
groups. In the crystal structure adjacent molecules are linked by C–H···O hydrogen bonds.

Graphical AbstractSummary sentence: Acetate and benzylidene protecting groups has been employed in the synthesis of 1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose (I) and its crystal structure has been determined from single crystal X-ray diffraction data.

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Keywords

1,2,3-Tri-O-acetyl-4,6-di-O-benzylidene-β-d-glucopyranose
 
4,6-O-benzylidene-glucopyranose moiety
 
6-OH groups
 
AbstractThe crystal
 
benzyl acetal
 
benzylic carbon
 
benzylidene
 
cell parameters
 
crystal structure adjacent molecules
 
C–H···O hydrogen bonds
 
glucopyranose
 
glucopyranose ring
 
glycosidic
 
Graphical AbstractSummary sentence
 
molecular structure
 
single crystal X-ray diffraction data
 
X-ray diffraction