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

반응식

HRID 466907 반응식
[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

참가 물질

4

반응물 2

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

생성물 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

시약·촉매·용매 1

HCID 24562Silver perchlorate촉매

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온도
-30 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f4731d97fd20421da235118fc7d50d68
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157116

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