Diethyl Ether → Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

HRID 466907

反応式

HRID 466907 の反応式
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([OH:25])[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:35][CH2:36][O:37][CH2:38][CH3:39]>Cl([O-])(=O)(=O)=O.[Ag+]>[CH2:36]([O:37][C@@H:38]1[C@@H:36]([O:37][CH2:38][C:39]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[C@H:35]([CH2:12][O:11][C:10](=[O:13])[CH3:9])[C@@H:15]([CH2:16][O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[O:25][C@@H:39]1[O:25][C@@H:15]1[C@@H:14]([CH2:26][O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C@H:16]1[O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:35]1[CH:31]=[CH:30][CH:29]=[CH:34][CH:33]=1

参加物

4

反応物 2

HCID 3283Diethyl EtherHCID 10983459(2R,3R,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol

生成物 1

HCID 54010971Methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethy-alpha-D-glucopyranosyl)-2,3,6-tri-O-benzyl-alpha-D-glucopyranoside

試薬・触媒・溶媒 1

HCID 24562Silver perchlorate触媒

反応条件

温度
-30 °C

実験手順

Ethereal silver perchlorate (0.08 M, 9.58 mL, 7.67 mmol) is added with stirring at -30° C. to a solution of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (2.592 g, 5.59 mmol), 2,3,6-tri-O-benzyl 1,4-dideoxy-4-acetyloxymethyl-D-glucopyranosyl chloride (3.661 g, 6.98 mmol) in ether (20 mL). The mixture is stirred 15 min at -30° C. and silver chloride precipitated. The mixture is filtered through a celite pad, the solids are washed with ether, the filtrate is concentrated under reduced pressure. The residue is dissolved in methylene chloride and the organic layer is washed successively with aqueous sodium thiosulfate and water. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure so as to afford a foam. Flash chromatography on silica gel and elution with a graded mixture of hexane and ethyl acetate will afford methyl 4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-acetyloxymethyl-α-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside as a foam.

後処理

  1. customsilver chloride precipitated
  2. filtrationThe mixture is filtered through a celite pad
  3. washthe solids are washed with ether
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. dissolutionThe residue is dissolved in methylene chloride
  6. washthe organic layer is washed successively with aqueous sodium thiosulfate and water
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure so as
  10. customto afford a foam
  11. washFlash chromatography on silica gel and elution
  12. additionwith a graded mixture of hexane and ethyl acetate

出典と根拠

ORDレコード
ord-f4731d97fd20421da235118fc7d50d68
出典データセット
uspto-grants-1992_10
特許番号
US05157116

関連ノート

読み込み中…