Water → HCID 86626525, compound

HRID 2106419Notes

Reaction equation

HRID 2106419 reaction equation
C1(C)C=CC(S(O[CH:11]2[CH2:15][CH2:14][O:13][CH2:12]2)(=O)=O)=CC=1.[CH2:17]([O:24][C@@H:25]1[C@@H:31]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@H:30]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@@H:29]([CH2:48][O:49][CH2:50][C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[O:28][C@@:26]1([C:57]1[CH:62]=[CH:61][C:60]([CH3:63])=[C:59]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([OH:71])=[CH:67][CH:66]=2)[CH:58]=1)[OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH2:17]([O:24][C@@H:25]1[C@@H:31]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C@H:30]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C@@H:29]([CH2:48][O:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[O:28][C@@:26]1([C:57]1[CH:62]=[CH:61][C:60]([CH3:63])=[C:59]([CH2:64][C:65]2[CH:70]=[CH:69][C:68]([O:71][CH:11]3[CH2:15][CH2:14][O:13][CH2:12]3)=[CH:67][CH:66]=2)[CH:58]=1)[OH:27])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 13837325Tetrahydrofuran-3-yl 4-methylbenzenesulfonateHCID 86600676HCID 86600676, compound

Product 1

HCID 86626525HCID 86626525, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g tetrahydrofuran-3-yl toluene-4-sulphonate are added to a mixture of 0.24 g 1-(2,3,4,6-tetra-O-benzyl-(β-D-glucopyranos-1-yl)-3-(4-hydroxy-benzyl)-4-methyl-benzene and 0.13 g caesium carbonate in 2.5 ml of dimethylformamide. The mixture is stirred for 4 h at 65° C., before water is added. It is extracted three times with ethyl acetate, the organic phase is dried over sodium sulphate and the solvent is removed. The residue is purified through silica gel purified (cyclohexane/ethyl acetate 10:1->4:1).

Workup

  1. additionis added
  2. extractionIt is extracted three times with ethyl acetate
  3. dry with materialthe organic phase is dried over sodium sulphate
  4. customthe solvent is removed
  5. customThe residue is purified through silica gel
  6. custompurified (cyclohexane/ethyl acetate 10:1->4:1)

Sources & evidence

ORD record
ord-ed3d2e1954a941239747411375315d7b
Source dataset
uspto-grants-2009_08
Patent number
US07579449B2

Reaction notes

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