HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylsilyl triflate → HCID 178508805, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylsilyl triflate | HCID 65367 | — |
| Reactant | 1-O-Acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose | HCID 10929242 | — |
| Reactant | 7-Aminothiazolo[4,5-d]pyrimidin-2(3H)-one | HCID 14505761 | — |
| Solvent | Hexamethyldisilazane | HCID 13838 | — |
| Product | HCID 178508805 | HCID 178508805 | 96.7% |
Reaction Steps
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:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04880784 |
| Source dataset | uspto-grants-1989_11 |
| ORD ID | ord-25bfca125e7a4dab9d7fb925519a3c33 |
| Source note | uspto-grants-1989_11 |