6743-67-5

Upstream product

• 4049-33-6 tetra-O-acetyl-β-D-xylopyranose 
• 3068-31-3 1-bromo-2,3,4-tri-O-acetyl-α-D-xylopyranose 
• 111-70-6 n-heptan1ol 
• 6743-60-8 1-heptyl 2,3,4-tri-O-acetyl-β-D-xylopyranoside 

Relevant academic research and scientific papers

Vitamin B12 and BF3-etherate as catalysts in synthesis of some C4-C12-alkyl β-D-xylopyranosides

Two methods are presented for synthesis of some C4-C 12-alkyl β-D-xylopyranosides. The first method is the vitamin B12-catalyzed reaction of glycosylation of acetobromoxylose with alkanols (ROH) (C4-C12). The reaction is carried out with 2 mol% of vitamin B12, with respect to xylosyl bromide, under argon at room temperature. Under these conditions peracetylated C4-C 12-alkyl β-D-xylopyranosides are obtained. Following chromatographic purification these products are deesterified with a mixture of methanol-triethylamine-water (2:1:1) to give corresponding alkyl β-D-xylopyranosides in 50-60% yield. In all cases 3,4-di-O-acetyl- D-xylal is obtained, as the product of reductive elimination of peracetylated xylosyl bromide (15-25%). The second method is synthesis of C4-C 12-alkyl β- D-xylopyranosides performed by glycosylation of corresponding alkanols with tetra-O-acetyl β- D-xylopyranose in the presence of BF3-etherate, as a Lewis acid catalyst. This glycosylation proceeds in only moderate yield (45-55%), but simplicity of this method and avoidance of expensive heavy metal catalysts make such procedure attractive.

Synthesis of C7-C16-alkyl glycosides: Part II - Synthesis of alkyl d-xylopyranosides in the presence of tin(IV) chloride as a Lewis acid catalyst

The Lewis acid catalyzed glycosylation reaction of β-peracetylated sugar derivatives (xylose) with fatty alkanols is used in a synthesis of C7-C16-alkyl D-xylopyranosides. The process occurs under the influence of tin(IV) chloride.