HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| Reactant | N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine | HCID 69534113 | — |
| Product | (2R,3R,4S,5R)-2-(6-[(2,2-Diphenylethyl)amino]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-9-yl)-5-(methoxymethyl)tetrahydro-3,4-furandiol | HCID 59975304 | 30.4% |
Reaction Steps
The title compound was prepared by a similar method to example 38 using N-(9-[(2R,3R,4R,5R)-3,4-bis{[tert-butyl(dimethyl)silyl]oxy}-5-(methoxymethyl)tetrahydro-2-furanyl]-2-{[2-(1-piperidinyl)ethoxy]methyl}-9H-purin-6-yl)-N-(2,2-diphenylethyl)amine (100 mg, 0.12 mmol) (preparation 29), and a 1M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (0.5 ml, 0.5 mmol). The compound was purified by column chromatography on silica gel eluting with a solvent system of dichloromethane:methanol:ammonia (95:5:0.5) to give the title compound (22 mg) as a gum. MS: 604 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06326359B1 |
| Source dataset | uspto-grants-2001_12 |
| ORD ID | ord-c04ecf9cf9a746be9b321560be48c284 |
| Source note | uspto-grants-2001_12 |