Benzyl Bromide → (2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran

HRID 1862756ノート

反応式

HRID 1862756 の反応式
[C:1]([O:4][C@H:5]1[C@H:18]([O:19][C:20](=O)[CH3:21])[C@H:17]([O:23][C:24](=O)[CH3:25])[C@H:16]([CH3:27])[O:15][C@@H:6]1[S:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=O)[CH3:2].C[O-].[Na+].CO.[H-].[Na+].[CH:35]1[CH:40]=[CH:39][C:38]([CH2:41]Br)=CC=1>CN(C=O)C.O.CCCCCC>[CH2:1]([O:4][C@H:5]1[C@H:18]([O:19][CH2:20][C:21]2[CH:5]=[CH:18][CH:17]=[CH:16][CH:27]=2)[C@H:17]([O:23][CH2:24][C:25]2[CH:41]=[CH:38][CH:39]=[CH:40][CH:35]=2)[C@H:16]([CH3:27])[O:15][C@@H:6]1[S:7][C:8]1[CH:9]=[CH:10][C:11]([CH3:14])=[CH:12][CH:13]=1)[C:2]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10000824p-Methylphenyl 2,3,4-Tri-O-acetyl-1-thio-beta-L-fucopyranosideHCID 23694274Sodium methanolate methanol

生成物 1

HCID 11071610(2S,3R,4R,5S,6R)-3,4,5-tris(benzyloxy)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran収率 152.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

p-Methylphenyl 2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranoside (ibid, Brukart, M. D. et al. 1997) (2.5 g, 6.31 mmol) was treated with NaOMe-MeOH. The product was further treated with 85% NaH (463 g, 22.7 mmol) and BnBr (5.8 mL, 37.86 mmol) in DMF (25 mL). After reaction was finished, hexane (30 mL) and water (300 mL) were added into the vigorously stirred solution. The solid product was filtered, washed with water (2×5 mL) and hexane-AcOEt (15:1, 2×5 mL). The crude product was suspended in a hot (70° C.) mixture of AcOEt-Hexane (10:1), and stirred for 10 min. cooled to rt, filtered to gave pure 50 (2.6 g, 76%) as solid: [α]D22 +8° (c, 0.5, CHCl3); HRMS (M+Cs) calcd for C34H36O4SCs 672.1290, found 672.1287.

後処理

  1. customAfter reaction
  2. filtrationThe solid product was filtered
  3. washwashed with water (2×5 mL) and hexane-AcOEt (15:1, 2×5 mL)
  4. additionThe crude product was suspended in a hot (70° C.) mixture of AcOEt-Hexane (10:1)
  5. filtrationfiltered

出典と根拠

ORDレコード
ord-8afa851ebd1049e7bbda5d0435b1d43b
出典データセット
uspto-grants-2003_03
特許番号
US06538117B1

反応ノート

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