(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester → (2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid

HRID 526280Notes

Reaction equation

HRID 526280 reaction equation
C([O:8][C:9](=[O:44])[CH2:10][O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][C@H:21]1[C@H:26]([NH:27][C:28](=[O:30])[CH3:29])[C@@H:25]([O:31][C:32](=[O:34])[CH3:33])[C@@H:24]([O:35][C:36](=[O:38])[CH3:37])[C@@H:23]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[O:22]1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[C:32]([O:31][C@H:25]1[C@@H:24]([O:35][C:36](=[O:38])[CH3:37])[C@@H:23]([CH2:39][O:40][C:41](=[O:43])[CH3:42])[O:22][C@@H:21]([O:20][CH2:19][CH2:18][O:17][CH2:16][CH2:15][O:14][CH2:13][CH2:12][O:11][CH2:10][C:9]([OH:44])=[O:8])[C@@H:26]1[NH:27][C:28](=[O:30])[CH3:29])(=[O:34])[CH3:33]

Participants

4

Reactant 1

HCID 58409195(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester

Product 1

HCID 58409186(2-{2-[2-((2R,3R,4R,5R,6R)-4,5-Diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acidYield 45.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The above prepared (2-{2-[2-((2R,3R,4R,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-ethoxy]-ethoxy}-ethoxy)-acetic acid benzyl ester (15.7 g, 25 mmol) was dissolved in 525 mL of ethyl acetate and hydrogenated over 1.6 g of Pd/C (10%) under 1 atm. of H2 at ambient temperature for 3 h. Filtration over Celite and evaporation of the solvent, followed by flash chromatography (SiO2, CH2Cl2/MeOH=80/20) gave 6.07 g of the title compound as a brownish gum. MS (ISP): 536.5 [M−H]−.

Workup

  1. filtrationFiltration
  2. customover Celite and evaporation of the solvent

Sources & evidence

ORD record
ord-c3038d61b1de45358d587b0a36d3069f
Source dataset
uspto-grants-2016_05
Patent number
US09345775B2

Reaction notes

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