Hydrochloric Acid → HCID 86605981, compound

HRID 2246496Notes

Reaction equation

HRID 2246496 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([C:34]#[C:35][Si](C(C)C)(C(C)C)C(C)C)=[CH:30][CH:29]=2)=[CH:23][C:22]=1[C@:46]1([O:64][C@H:63]([CH2:65][O:66]C(=O)C)[C@@H:58]([O:59]C(=O)C)[C@H:53]([O:54]C(=O)C)[C@H:48]1[O:49]C(=O)C)[OH:47].[OH-].[K+].Cl>O1CCCC1.CO>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]2[CH:29]=[CH:30][C:31]([C:34]#[CH:35])=[CH:32][CH:33]=2)=[CH:23][C:22]=1[C@:46]1([O:64][C@H:63]([CH2:65][OH:66])[C@@H:58]([OH:59])[C@H:53]([OH:54])[C@H:48]1[OH:49])[OH:47]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 2724141Tetrabutylammonium FluorideHCID 86605982HCID 86605982, compound

Product 1

HCID 86605981HCID 86605981, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.78 mL of a 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran are added to a solution of 0.55 g 1-methoxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-4-(4-triisopropylsilylethynyl-benzyl)-benzene in 2 mL tetrahydrofuran. The solution is stirred for 30 min at ambient temperature and then diluted with 4 mL methanol. 0.85 mL of 4 M potassium hydroxide solution are added and the resulting solution is stirred for an additional 30 min at ambient temperature. The reaction solution is neutralized with 1 M hydrochloric acid and concentrated in vacuo. The residue is combined with brine and extracted with ethyl acetate. The combined organic extracts are dried over sodium sulfate and the solvent is evaporated. The residue is chromatographed over silica gel (dichloromethane/methanol 9:1->2:1).

Workup

  1. stirringthe resulting solution is stirred for an additional 30 min at ambient temperature
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried over sodium sulfate
  5. customthe solvent is evaporated
  6. customThe residue is chromatographed over silica gel (dichloromethane/methanol 9:1->2:1)

Sources & evidence

ORD record
ord-043c13f11e88491c8bd1e42f792a005f
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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