2,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purine → HCID 22858292, compound

HRID 375148Notes

Reaction equation

HRID 375148 reaction equation
Cl.[NH2:2][C@H:3]([CH3:15])[CH2:4][S:5][C:6]1[O:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1.C([O:19][C@@H:20]1[C@H:24]([O:25]C(=O)C)[C@@H:23]([CH2:29][O:30]C(=O)C)[O:22][C@H:21]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][C:37]([Cl:44])=[N:38][C:39]=2Cl)(=O)C.C[O-].[Na+]>CO>[O:7]1[C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=[C:6]1[S:5][CH2:4][C@H:3]([NH:2][C:39]1[C:40]2[N:41]=[CH:42][N:34]([C:35]=2[N:36]=[C:37]([Cl:44])[N:38]=1)[C@@H:21]1[O:22][C@H:23]([CH2:29][OH:30])[C@@H:24]([OH:25])[C@H:20]1[OH:19])[CH3:15]

Participants

5

Reactant 3

HCID 102530272,6-Dichloro-9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)purineHCID 10942334Sodium MethoxideHCID 677713162-[(R)-2-amino-1-propylthio]benzoxazole hydrochloride

Product 1

HCID 22858292HCID 22858292, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was prepared essentially according to method A as described above in Example 1 by reacting 2-[(R)-2-amino-1-propylthio]benzoxazole hydrochloride [prepared by alkylation of 2-mercaptobenzoxazole (3.5 g, 23 mmol) using methanesulphonic acid, 2-[(R)-N-tert-butyloxycarbonylamino]-1-propyl ester (7.2 g, 30 mmol) followed by acidic hydrolysis] (1.7 g, 6 mmol) with 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2,6-dichloro-9H-purine (2.7 g, 6.0 mmol), followed by deacylation of the purified product using sodium methoxide in methanol. This provided the title N-[(R)-1-(2-benzoxazolyl)thio2-propyl]-2-chloroadenosine (0.37 g, 28%) as a foam after column chromatography. 1H NMR (DMSO-d6) δ 1.38 (3H, d, --CHCH3), 3.40-3.75 (4H, m, H-5'a and H-5'b and --CH2 --), 3.94 (1H, q, H-4), 4.12 (1H, q, H-3'), 4.52 (1H, m, H-2'), 5.06 (1H, t, 5'-OH), 5.22, 5.49 (2H, 2d, 2'- and 3'-OH), 5.82 (1H, d, H-1'), 7.26-7.35 (2H, m, Ar-H), 7.53-7.64 (2H, m, Ar-H), 8.39 (1H, s, H-8), 8.48 (1H, d, --NH).

Workup

  1. customThe title compound was prepared essentially

Sources & evidence

ORD record
ord-35aa6b2e77c64900a3e75b6678bca1e3
Source dataset
uspto-grants-1996_01
Patent number
US05484774

Reaction notes

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