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Imidazole → 1-[5-O-Benzoyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl]thymine

HRID 215730
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HRID 215730 반응식
[C:1]([O:9][CH2:10][C@@:11]1([C:33]#[C:34][Si](C)(C)C)[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[O:25][Si](C(C)(C)C)(C)C)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.CC([Si](Cl)(C1C=CC=CC=1)C1C=CC=CC=1)(C)C>CN(C=O)C>[C:1]([O:9][CH2:10][C@@:11]1([C:33]#[CH:34])[O:15][C@@H:14]([N:16]2[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]2=[O:18])[CH2:13][C@H:12]1[OH:25])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 115269021-[5-O-Benzoyl-3-O-(t-butyldimethylsilyl)-2-deoxy-4-(trimethylsilyl)ethynyl-beta-D-threo-pentofuranosyl]thymine

생성물 1

HCID 115887611-[5-O-Benzoyl-2-deoxy-4-ethynyl-beta-D-threo-pentofuranosyl]thymine수율 85.2%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

실험 절차

A mixture of 3 (10.35 g, 60.1 mmol), imidazole (8.18 g, 120.2 mmol), and TBDPSCl (15.6 ml, 60.1 mmol) in DMF (40 ml) was stirred for 16 h at room temperature under positive pressure of dry Ar. The mixture was partitioned between EtOAc and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4) and evaporated. The resulting syrupy residue was treated with MeOH (ca. 40 ml) to give the precipitated 4. This procedure was repeated further 3 times to give 4 (18.97 g, 77%) as a white solid.

후처리

  1. customThe mixture was partitioned between EtOAc and sat. aqueous NaHCO3
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated
  4. additionThe resulting syrupy residue was treated with MeOH (ca. 40 ml)
  5. customto give the
  6. customprecipitated 4

출처 및 근거

ORD 기록
ord-8ac37bfb6e1e4266b206f134bbb7b67c
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08193165B2

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