Hydrochloric Acid → 1-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine

HRID 6778

반응식

HRID 6778 반응식
C([O:4][C@@H:5]1[C@@H:9]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([CH2:28][O:29]C(=O)C2C=CC=CC=2)([CH2:18][O:19]C(=O)C2C=CC=CC=2)[O:7][C@H:6]1[N:38]1[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]1=[O:40])(=O)C.C[O-].[Na+].Cl>CO>[CH2:11]([O:10][C@H:9]1[C:8]([CH2:18][OH:19])([CH2:28][OH:29])[O:7][C@@H:6]([N:38]2[CH:46]=[C:44]([CH3:45])[C:42](=[O:43])[NH:41][C:39]2=[O:40])[C@@H:5]1[OH:4])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 107940411(2-O-Acetyl5-O-benzoyl-4-C-benzoyloxymethyl-3-O-benzyl-beta-D-xylofuranosyl)thymineHCID 10942334Sodium Methoxide

생성물 1

HCID 106910381-(3-O-Benzy-4-hydroxymethyl-beta-D-xylofuranosyl)thymine수율 91%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of nucleoside 4 (9.00 g, 0.014 mol) in methanol (130 cm3) was added sodium methoxide (3.87 g, 0.0716 mol). The reaction mixture was stirred at room temperature for 4 h and then neutralised with dilute hydrochloric acid. The mixture was evaporated to dryness under reduced pressure followed by coevaporation using toluene (15 cm3×3). The residue was purified by silica gel column chromatography using dichloromethane/methanol (4–1 5% methanol, v/v) as eluent to give nucleoside triol 5 (4.82 g, 89%) as a white solid material after evaporation of the solvents under reduced pressure.

후처리

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-5bfff2d50122426db511b3e9f2d81ec6
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084125B2

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