Process for the preparation of 2-deoxy-2,2-difluoro-.beta.-D-rib

Details Process for the preparation of 2-deoxy-2,2-difluoro-.beta.-D-rib Process for the preparation of 2-deoxy-2,2-difluoro-.beta.-D-rib

1996-05-16

1997-03-04

Wilson, James O.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 184, 536 185, C07H 100, C07H 308

Patent

active

056080433

ABSTRACT:
A process for the preparation of 1-(2'-deoxy-2', 2'-difluoro-D-ribo-pentofuranosyl)-cytosine (VI) from 2-deoxy-2,2-difluoro-.beta.-D-ribo-pentopyranose (I). The process uses a tritylation reaction (Step 3) for preparing 2-deoxy-2,2-difluoro-5-O-triphenylmethyl-ribo-pentofuranose (II) as a key intermediate. The 1-(2'-deoxy-2', 2'-difluoro-D-ribo-pentofuranosyl)-cytosine (VI) is an antiviral and anti-cancer agent.

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patent: 5430026 (1995-07-01), Hertel et al.
patent: 5434254 (1995-07-01), Chou et al.
Helferich, B., "Trityl Ethers of Carbohydrates", in Adv. Carb. Chem., 3, 79-III (1948).
Chou, T.S., et al., Synthesis, 6, 565-570 (1992).
Hertel, L.W., et al., J. Org. Chem., 53, 2406-2409 (1988).

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