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

HRID 1910652노트

반응식

HRID 1910652 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c8fd9f9f100f4ea9948140cd60f7baec
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604004B2

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