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Synthesis of the 3-methyl Ether and 4-deoxy Derivatives of 4-cyanophenyl 1,5-dithio-beta-D-xylopyranoside (Beciparcil)

Synthesis of the 3-methyl Ether and 4-deoxy Derivatives of 4-cyanophenyl 1,5-dithio-beta-D-xylopyranoside (Beciparcil)

Y Li, D Horton, V Barberousse, S Samreth, F Bellamy

Carbohydr Res. 1999 Mar 31;316(1-4):104-11.

PMID: 10420590

Abstract:

Treatment of the 2,3-isopropylidene acetal of the title dithioxyloside with 2,4,5-triiodoimidazole-PPh3 caused replacement of the 4-hydroxyl group by iodine to afford 82% of the 4-axial iodide 6, converted by base into 4-cyanophenyl 2,3-O-isopropylidene-1,5-dithio-beta-D-glycero-pent-3-enopyranoside++ + (8). Acid treatment of 8 gave 87% of the deacetonated glycos-3-ulose, borohydride reduction of which afforded 63% of 4-cyanophenyl 4-deoxy-1,5-dithio-alpha-L-threo-pentopyranoside (3), together with 27% of the 3-axial epimer. The 3-methyl ether of the title dithioxyloside was satisfactorily prepared via 2,4-protection as the cyclic phenylboronate, methylation, and deprotection; alternative strategy via the 2,4-bis(triisopropylsilyl) ether was complicated because of silyl-group migration under methylation conditions.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931178	1-(triisopropylsilyl)pyrrole-3-boronic acid			Price

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