Trimethylsilyl triflate → HCID 178508805, compound

HRID 1638535Notes

Reaction equation

HRID 1638535 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][C:9](=[O:11])[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O[CH:16]1[O:38][C@H:37]([CH2:39][O:40][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@@H:27]([O:28][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:17]1[O:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=O)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C[Si](N[Si](C)(C)C)(C)C>[NH2:1][C:2]1[N:7]=[CH:6][N:5]([C@@H:16]2[O:38][C@H:37]([CH2:39][O:40][C:41](=[O:48])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C@@H:27]([O:28][C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C@H:17]2[O:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:4]2=[N:8][C:9](=[O:11])[S:10][C:3]=12

Participants

5

Reactant 3

HCID 65367Trimethylsilyl triflateHCID 109292421-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranoseHCID 145057617-Aminothiazolo[4,5-d]pyrimidin-2(3H)-one

Product 1

HCID 178508805HCID 178508805, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 13838HexamethyldisilazaneSolvent

Procedure

Compound 30 (460 mg, 2.7 mmol) was glycosylated in the same manner as that used to prepare 6, requiring HMDS (30 mL), benzoyl-blocked sugar (5: 1.5 g, 3.0 mmol), and TMS-triflate (0.76 mL, 3.9 mmol). The reaction mixture was allowed to stir overnight at room temperature and was then worked up as described for 6 to yield 1.6 g (95%) of 31 isolated as a foam: UV λmaxMeOH) 230 nm (ε), 310 (): 1H NMR (DMSO-d6 9 δ6.45 (d, J=2.73 Hz, 1H, C1,H), 7.4-8.0 (m, 15 H, benzoyl aromatics), 8.59 (s, 1H, C5H), and other sugar protons C31H24N4O8S: C, 60.78: H, 3.95: N, 9.15: S, 5.23. Found:

Workup

  1. customto prepare 6

Sources & evidence

ORD record
ord-25bfca125e7a4dab9d7fb925519a3c33
Source dataset
uspto-grants-1989_11
Patent number
US04880784

Reaction notes

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