p-Toluenesulfonic acid monohydrate → (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-ethoxyphenyl]-D-glucitol

HRID 1375994Notes

Reaction equation

HRID 1375994 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:13]([O:15][C:16]1[CH:35]=[CH:34][C:19]([CH2:20][C:21]2[CH:30]=[C:29]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=[CH:28]3)[C:22]=2C(O)=O)=[CH:18][C:17]=1[C@H:36]1[C@@H:41]([O:42]C(=O)C)[C@@H:40]([O:46]C(=O)C)[C@@H:39]([O:50]C(=O)C)[C@@H:38]([CH2:54][O:55]C(=O)C)[O:37]1)[CH3:14]>>[CH:22]1[C:23]2[C:29]([CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:30][C:21]=1[CH2:20][C:19]1[CH:34]=[CH:35][C:16]([O:15][CH2:13][CH3:14])=[C:17]([C@@H:36]2[O:37][C@H:38]([CH2:54][OH:55])[C@@H:39]([OH:50])[C@H:40]([OH:46])[C@H:41]2[OH:42])[CH:18]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 693824782-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid

Product 1

HCID 58786129(1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-ethoxyphenyl]-D-glucitolYield 84.6%

Procedure

p-Toluenesulfonic acid monohydrate (40 mg) was added to a suspension of 2-(4-ethoxy-3-[(2S,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]tetrahydro-2H-pyran-2-yl]benzyl)azulene-1-carboxylic acid (0.36 g) inbenzene (10 ml) and the mixture was refluxed with heating for 15 minutes. The reaction mixture was concentrated. The residue was purified by silica gel column chromatography (chloroform-methanol) to obtain (1S)-1,5-anhydro-1-[5-(azulen-2-ylmethyl)-2-ethoxyphenyl]-D-glucitol (203 mg).

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 15 minutes
  3. concentrationThe reaction mixture was concentrated
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-9e7fe0ccef8c42ca87b91a130914f4af
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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