(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol → (1S)-1,5-anhydro-1-[5-[4-[2-[[(2-hydroxy-1,1-dimethylethyl)aminocarbonyl]amino]ethyl]benzyl]-2-hydroxy-4-methylphenyl]-D-glucitol

HRID 1009890Notes

Reaction equation

HRID 1009890 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[CH:45]=[C:44]([CH2:46][C:47]2[CH:52]=[CH:51][C:50]([CH2:53][CH2:54][NH:55][C:56]([NH:58][C:59]([CH3:63])([CH3:62])[CH2:60][OH:61])=[O:57])=[CH:49][CH:48]=2)[C:43]([CH3:64])=[CH:42][C:41]=1[O:65]CC1C=CC=CC=1)C1C=CC=CC=1>[OH-].[Pd+2].[OH-].CO>[OH:61][CH2:60][C:59]([NH:58][C:56]([NH:55][CH2:54][CH2:53][C:50]1[CH:51]=[CH:52][C:47]([CH2:46][C:44]2[C:43]([CH3:64])=[CH:42][C:41]([OH:65])=[C:40]([C@@H:10]3[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]3[OH:8])[CH:45]=2)=[CH:48][CH:49]=1)=[O:57])([CH3:62])[CH3:63]

Participants

4

Reactant 1

HCID 86638449(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl)-D-glucitol

Product 1

HCID 67304774(1S)-1,5-anhydro-1-[5-[4-[2-[[(2-hydroxy-1,1-dimethylethyl)aminocarbonyl]amino]ethyl]benzyl]-2-hydroxy-4-methylphenyl]-D-glucitolYield 58%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (4 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[2-[[[(2-hydroxy-1,1-dimethylethyl)amino]carbonyl]amino]ethyl]benzyl]-4-methylphenyl]-D-glucitol (0.184 mg, 0.190 mmol) was added 20% palladium hydroxide (0.180 g), and the mixture was stirred under a hydrogen atmosphere at room temperature overnight. The reaction solution was filtered through celite and evaporated under reduced pressure. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=17:3) to obtain the title compound (57 mg, 58%) as a colorless powder. NMR data and MS data of the compound are shown in Table 1.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. customevaporated under reduced pressure
  3. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=17:3)

Sources & evidence

ORD record
ord-77ec8803dd5d4dc1aee73390bd751539
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

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