Triethylamine → 1-O-methyl 5-(t-butyldiphenylsilyl)-beta-D-ribofuranoside

HRID 965189

반응식

HRID 965189 반응식
[CH3:1][O:2][CH:3]1[O:7][CH:6]([CH2:8][OH:9])[CH:5]([OH:10])[CH:4]1[OH:11].C(N(CC)CC)C.[C:19]([Si:23]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)Cl)([CH3:22])([CH3:21])[CH3:20]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Si:23]([CH:8]([OH:9])[C@H:6]1[O:7][C@@H:3]([O:2][CH3:1])[C@H:4]([OH:11])[C@@H:5]1[OH:10])([C:19]([CH3:22])([CH3:21])[CH3:20])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 255320beta-D-Ribofuranoside, methyl

생성물 1

HCID 186611941-O-methyl 5-(t-butyldiphenylsilyl)-beta-D-ribofuranoside수율 54.8%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of methyl-β-D-ribofuranoside (460 mg, 2.8 mmol, Sigma, St. Louis, Mo.) and anhydrous methylene chloride (20 ml) were added triethylamine (0.468 ml, 3.36 mmol), t-butyldiphenylchlorosilane (0.9 ml, 3.46 mmol), and DMAP (13.7 mg, 0.112 mmol) successively at room temperature. The reaction mixture was stirred at room temperature for 18 h under nitrogen. It was washed with water (20 ml), saturated ammonium chloride (20 ml), and brine (20 ml), dried over anhydrous MgSO4, filtered, and concentrated to dryness. The residue was separated by silica gel column chromatography (CHCl3 --MeOH, 50:1) to yield 1-O-methyl 5-(t-butyldiphenylsilyl)-β-D-ribofuranoside (618 mg, 54.8%) as a thick syrup. 1H NMR (DMSO-d6) δ0.96 (s, 9H, t-Bu), 3.22 (s, 3H, --OCH3), 3.61 (dd, J=11.0 and 5.3 Hz, 1H), 3.74 (d, J=4.4 Hz, 1H), 3.81 (dd, J=11.0 and 2.7 Hz, 1H), 3.90 (m, 1H), 4.00 (m, 1H), 4.68 (s, 1H, H-1'), 4.84 (br s, 1H, exchangeable with D2O, OH), 5.05 (br s, 1H, exchangeable with D2O, OH), 7.45 and 7.67 (m, 10H, Ph2).

후처리

  1. washIt was washed with water (20 ml), saturated ammonium chloride (20 ml), and brine (20 ml)
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was separated by silica gel column chromatography (CHCl3 --MeOH, 50:1)

출처 및 근거

ORD 기록
ord-cc6db687f40b491d97054a1245c8cf35
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773423

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