Uridine → Uridine, 2',3'-dideoxy-3'-(hydroxymethyl)-

HRID 1288796Notes

Reaction equation

[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)[C@H]1O.N[C@H:19]1[C@H:24]([OH:25])[C@@H:23]([CH2:26][OH:27])[O:22][C@@H:21]([N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:20]1>>[OH:25][CH2:24][C@@H:19]1[C@@H:23]([CH2:26][OH:27])[O:22][C@@H:21]([N:28]2[CH:35]=[CH:34][C:32](=[O:33])[NH:31][C:29]2=[O:30])[CH2:20]1

Participants

Reactant 2

HCID 6029Uridine

HCID 15277067HCID 15277067, compound

Product 1

HCID 452407Uridine, 2',3'-dideoxy-3'-(hydroxymethyl)-

Procedure

Med. Chem. Vol 22, 1979, 518-525 describes the synthesis of methyl 2,3-dideoxy-3-C-(hydroxymethyl)-β-D-erythropentofuranoside as well as the corresponding dibenzyl- and dibenzoyl derivative. The chloro derivative 5-0-benzoyl-3-C-[(benzoyloxy)methyl)]-2,3-dideoxy-D-erythro-pentafuranosyl chloride was coupled with 2-acetamido-6-chloropurine. The product was processed further to give the two anomers of 2-amino-9-[2,3-dideoxy-3-C-3-(hydroxymethyl)-D-erythro-pentofuranosyl]-9H-purine-6(1H)-thione which were tested for antitumor activity. The synthesis of 2,3'-dideoxy-3'(R)-hydroxymethyl uridine has been described in Nucleosides & Nucleotides 1 (1982) 263-273. Uridine was converted to 1-(3-amino-2,3-dideoxy-β-D-glucopyranosyl)uracil via a multistage sequence, which was further reacted via ring contraction, epimerization and reduction to give 2',3'-dideoxy-3'(R)-hydroxymethyl uridine.

Workup

customwas further reacted via ring contraction, epimerization and reduction

Sources & evidence

ORD record: ord-45dd8aaac64f4838a520795a3974cc9c
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05747473

Reaction notes

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