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2,4,6-Trimethylpyridine → Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl)-2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

HRID 466905
Notes
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Reaction equation

HRID 466905 reaction equation
[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]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@@H:14]([CH2:33][OH:34])[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O:38][C@H:39]1[C@@H:44]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:43][C@H:42](Cl)[C@H:41]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@H:40]1[O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1)(=[O:37])[CH3:36].CC1C=C(C)C=C(C)N=1>CCOCC.Cl([O-])(=O)(=O)=O.[Ag+]>[C:35]([O:38][C@H:39]1[C@@H:44]([CH2:45][O:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[O:43][C@H:42]([O:34][CH2:33][C@H:14]2[O:13][C@H:10]([O:11][CH3:12])[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:15]2[O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@H:41]([O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C@H:40]1[O:63][CH2:64][C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)(=[O:37])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 79532,4,6-TrimethylpyridineHCID 11190476Methyl 2,3,4-tri-O-benzyl-alpha-D-glucopyranosideHCID 544033654-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl chloride

Product 1

HCID 53849711Methyl 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl)-2,3,4-tri-O-benzyl-alpha-D-glucopyranoside

Reagents, catalysts & solvents 2

HCID 24562
Silver perchlorate
Catalyst
HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-30 °C

Procedure

Ethereal silver perchlorate (0.08 M, 76.9 mL, 6.15 mmol) is added with stirring at -30° C. to a solution of methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside (2.078 g, 4.48 mmol), 4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl chloride (2.859 g, 5.6 mmol) and 2,4,6-trimethylpyridine (0.81 mL, 6.15 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 6-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-galactopyranosyl)-2,3,4-tri-O-benzyl-α-D-glucopyranoside as a foam.

Workup

  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

Sources & evidence

ORD record
ord-ea2e577b99044a9fbcce7033137ab7e9
Source dataset
uspto-grants-1992_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05157116

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes