HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid → N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-3-O-tetrahydropyranyl-beta-D-erythro-pentofuranosyl]-guanine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid | HCID 6101 | — |
| Reactant | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Reactant | N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-beta-D-erythro-pentofuranosyl]guanine | HCID 137227857 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | N2-Methoxytrityl-9-[(2R)-2-deoxy-2-C-ethynyl-2-fluoro-5-O-tert-butyldimethylsilyl-3-O-tetrahydropyranyl-beta-D-erythro-pentofuranosyl]-guanine | HCID 137227859 | — |
Reaction Steps
To a stirred solution of 13 (0.8 mmol), in anh THF (20 ml/mmol), at room temperature, was added p-toluen sulfonic acid (0.12 mmol) and dihydropyran (2 ml/mmol). The reaction mixture was stirred at room temperature for 3 days and neutralized with TEA. The mixture was diluted with DCM, washed twice with H2O. The organic phase was dried over Na2SO4, filtered and evaporated. The crude material was purified by silica gel chromatography (DCM/MeOH) to yield the title compound. Molecular Formula C43H52FN5O6Si. Scan ES+ 780 (M+H)+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07902202B2 |
| Source dataset | uspto-grants-2011_03 |
| ORD ID | ord-1003f0e40c94475c9ca449659a5815d6 |
| Source note | uspto-grants-2011_03 |