Benzyl Bromide → Phenyl 3-O-benzyl-1-thio-beta-D-galactopyranoside

HRID 1910652ノート

反応式

HRID 1910652 の反応式
[S:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].C([Sn](=O)CCCC)CCC.[CH:29]1[CH:34]=[CH:33][C:32]([CH2:35]Br)=[CH:31][CH:30]=1>CO.[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[CH2:35]([O:6][C@H:5]1[C@@H:7]([OH:8])[C@@H:9]([CH2:11][OH:12])[O:10][C@@H:2]([S:1][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@@H:3]1[OH:4])[C:32]1[CH:33]=[CH:34][CH:29]=[CH:30][CH:31]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 61221Dibutyltin oxideHCID 2802071phenyl thio-beta-D-galactopyranoside

生成物 1

HCID 86653955Phenyl 3-O-benzyl-1-thio-beta-D-galactopyranoside収率 68%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 887Methanol溶媒

実験手順

A solution of phenyl 1-thio-β-D-galactopyranoside (2.1) (3.00 g, 11.0 mmol) and dibutyltin oxide (3.00 g, 12.1 mmol) in dry methanol (80 ml) was refluxed for 2 hours to produce a clear mixture. The solvent was then evaporated under reduced pressure. The resultant residue was dissolved in dry benzene (80 mL) followed by the addition of Bu4NBr (3.90 g, 12.11 mmol) and BnBr (1.3 ml, 12.1 mmol). The mixture was refluxed overnight. After cooling to room temperature, the mixture was concentrated and the residue was purified by silica gel chromatography (50% EtOAc/petroleum ether) to afford the title compound (2.71 g, 7.48 mmol, 67%). 1H NMR (400 MHz, CDCl3): δ 7.60-7.20 (m, 10H, PhH), 4.77, 4.68 (ABq, J=11.7 Hz, 1H each, OCH2Ph), 4.59 (d, J=9.5 Hz, 1H, H-1), 4.08 (d, J=2.6 Hz, 1H, H-4), 3.76 (dd, J=9.5, 9.5 Hz, 1H, H-2), 3.75 (dd, J=11.4, 5.8 Hz, 1H, H-6), 3.70 (dd, J=11.4, 5.8 Hz, 1H, H-6), 3.50 (dd, J=5.8, 5.8 Hz, 1H, H-5), 3.41 (dd, J=9.5, 2.6 Hz, 1H, H-3); 13C NMR (100 MHz, CDCl3): δ 131.0, 128.6, 128.1, 127.8, 127.4, 126.8, 89.1, 82.5, 79.2, 71.5, 69.0, 66.2, 61.4; HRMS calcd for C19H26O5SN [M+NH4]+: 380.1532. found 380.1527.

後処理

  1. customto produce a clear mixture
  2. customThe solvent was then evaporated under reduced pressure
  3. dissolutionThe resultant residue was dissolved in dry benzene (80 mL)
  4. temperatureThe mixture was refluxed overnight
  5. concentrationthe mixture was concentrated
  6. customthe residue was purified by silica gel chromatography (50% EtOAc/petroleum ether)

出典と根拠

ORDレコード
ord-c8fd9f9f100f4ea9948140cd60f7baec
出典データセット
uspto-grants-2013_12
特許番号
US08604004B2

反応ノート

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