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

HRID 965189

反応式

HRID 965189 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cc6db687f40b491d97054a1245c8cf35
出典データセット
uspto-grants-1998_06
特許番号
US05773423

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