Adenosine → 9-[(2R,5S)-5-(hydroxymethyl)thiolan-2-yl]-3H-purin-6-one

HRID 2260893Notes

Reaction equation

HRID 2260893 reaction equation
[CH:1]1([N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3Cl)[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1.[C@@H]1(N2C3N=CN=C(N)C=3N=C2)O[C@H](CO)[C@@H](O)[C@H]1[OH:20]>CC[N+](CC)(CC)CC.[Br-]>[C@@H:1]1([N:8]2[C:9]3[N:10]=[CH:11][N:12]=[C:13]([OH:20])[C:14]=3[N:15]=[CH:16]2)[S:5][C@H:4]([CH2:6][OH:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 60961AdenosineHCID 151261019-(4-Thio-2,3-dideoxy-D-ribofuranosyl)-6-chloropurine

Product 1

HCID 1785209669-[(2R,5S)-5-(hydroxymethyl)thiolan-2-yl]-3H-purin-6-oneYield 79%

Reagents, catalysts & solvents 1

HCID 6285Tetraethylammonium BromideCatalyst

Procedure

To a solution of the α/β anomers of 20 (82 mg, 0.3 mmol) in 20 mL of a 0.75 M TEAB buffer was added 3 μL adenosine deaminase. The reaction was stirred 34 h followed by lyophilization. The residue was purified by preparative TLC with 6:1 chloroform-methanol containing 1% acetic acid. The crude product was recrystallized from methanol/carbontetrachloride to give 30.5 mg (79%) of 21; mp. 195°-197 C.; [α]D25 -13.9° (c=0.1, H2O); FAB MS 253 (M+H)+ ; 1H NMR (D20) δ 8.5 (s, 1, H-2), 8.2 (s, 1, H-8), 6.2 (m, 1, 1'-H), 3.95 (m, 1, 5'-H), 3.8 (m, 2, 4'-H, 5'-H), 2.5 (m, 2, 2'-H's), 2.3 (m, 1, 3'-H), 1.9 (m, 1, 3'-H).

Workup

  1. customThe residue was purified by preparative TLC with 6:1 chloroform-methanol containing 1% acetic acid
  2. customThe crude product was recrystallized from methanol/carbontetrachloride

Sources & evidence

ORD record
ord-01e08424a7384eeb86036691af8044a4
Source dataset
uspto-grants-1995_12
Patent number
US05478928

Reaction notes

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