Tin tetrachloride → Xylocytidine

HRID 542708Notes

Reaction equation

HRID 542708 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C(O[C@H:13]1[O:35][C@H:34]([CH2:36][O:37]C(=O)C2C=CC=CC=2)[C@H:24]([O:25]C(=O)C2C=CC=CC=2)[C@H:14]1[O:15]C(=O)C1C=CC=CC=1)(=O)C.[Sn](Cl)(Cl)(Cl)Cl>C(#N)C>[C@@H:13]1([N:1]2[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]2=[O:3])[O:35][C@H:34]([CH2:36][OH:37])[C@H:24]([OH:25])[C@H:14]1[OH:15]

Participants

5

Reactant 3

HCID 24287Tin tetrachloride2×HCID 12671511HCID 12671511, compoundHCID 178418229Cytosine

Product 1

HCID 160696Xylocytidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

One equivalent of cytosine is condensed with one equivalent of 1-O-acetyl-2,3,5-tri-O-benzoyl-α-D-xylofuranose at ambient temperature, in anhydrous acetonitrile, in the presence of tin tetrachloride, SnCl4 (2 equivalents); the compound obtained is purified by chromatography on a silica column and debenzoylated using a methonal solution saturated with ammonia gas. This gives 1-(β-D-xylofuranosyl)-cytosine.

Workup

  1. customthe compound obtained
  2. customis purified by chromatography on a silica column

Sources & evidence

ORD record
ord-41af0156057c4f2db01f4589ad21aad4
Source dataset
uspto-grants-1987_04
Patent number
US04659698

Reaction notes

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