Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
Acetic Acid → 1-[4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|---|---|---|
| 반응물 | Acetic Acid | HCID 176 | — |
| 반응물 | Formaldehyde | HCID 712 | — |
| 반응물 | Sodium Hydroxide | HCID 14798 | — |
| 반응물 | Acetic Acid 4-(tert-butyl-diphenyl-silanyloxy)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5-formyl-tetrahydro-furan-3-yl Ester | HCID 86594161 | — |
| 용매 | 1,4-Dioxane | HCID 31275 | — |
| 생성물 | 1-[4-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-5,5-bis-hydroxymethyl-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione | HCID 66772729 | — |
반응 단계
Hydroxymethylation of the 5′-aldehyde is performed as per the method of Cannizzaro which is well documented in the literature (Jones, G. H., et. al., J. Org. Chem. 1979, 44, 1309-1317). These conditions are expected to additionally remove the 2′-O-acetyl group. Generally, Briefly, formaldehyde (2.0 eq., 37% aq.) and NaOH (1.2 eq., 2 M) is added to a solution of Compound 10 in 1,4-dioxane. After stirring at room temperature for several hours, this mixture is neutralized with acetic acid, evaporated to dryness, suspended in methanol, and evaporated onto silica gel. The resulting mixture is added to the top of a silica gel column and eluted using an appropriate solvent system to give Compound 11.
출처 및 근거
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 특허 번호 | US07696345B2 |
| 출처 데이터셋 | uspto-grants-2010_04 |
| ORD ID | ord-06ada91244b84992a9a96ee57f14e80c |
| 출처 메모 | uspto-grants-2010_04 |