178757-74-9

Upstream product

• 55287-65-5 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-glucopyranosyl chloride 
• 13036-15-2 1,3,4,6-tetra-O-acetyl-β-D-glucopyranose 

Downstream Products

• 178757-76-1 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-2-acetoxymethyl-5-((2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-benzyloxy-tetrahydro-pyran-2-yloxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester 

Relevant academic research and scientific papers

A serendipitous synthesis of cyclokojibiose

The fully protected kojibiosyl trichloroacetimidate 5 undergoes intramolecular cyclization accompanied by expulsion of the O-benzyl protecting group upon activation by a Lewis-acid to give the symmetrical, tricyclic compound 6 which is the first member of an as yet unreported group of cyclooligosaccharides.

Synthesis and X-ray crystallographic study of cyclobis-(1 → 2)-α-D-glucopyranosyl peracetate

Treatment of O-(3,4,6-tri-O-acetyl-2-O-benzyl- α-D-glucopyranosyl)-(1 → 2)-3,4,6-tri-O-acetyl-α-D-glucopyranosyl trichloroacetimidate with BF3·Et2O gave a high yield of the peracetate of cyclobis-(1 → 2)-α-D-glucopyranosyl (6). Compound 6 crystallizes in the space group P21, [a = 6.888(2), b = 24.771(5), c = 9.105(2) A, β = 111.49(2)°, Z = 2] and shows a high degree of symmetry. In 6 the two α-D-glucopyranosyl residues are in a slightly distorted chair conformation. The glucose moieties are interconnected by a 1,4-dioxane moiety which is in a boat conformation, with the anomeric carbon atoms in the bow positions.