(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol → (1S)-1,5-anhydro-1-[2-hydroxy-5-[4-[4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobutyl]benzyl]-4-methylphenyl]-D-glucitol

HRID 1009882Notes

Reaction equation

HRID 1009882 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](/[CH:53]=[CH:54]/[CH2:55][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>[Pd].CO>[OH:65][C:41]1[CH:42]=[C:43]([CH3:64])[C:44]([CH2:46][C:47]2[CH:48]=[CH:49][C:50]([CH2:53][CH2:54][CH2:55][C:56]([NH:58][C:59]([CH3:63])([CH3:62])[CH2:60][OH:61])=[O:57])=[CH:51][CH:52]=2)=[CH:45][C:40]=1[C@@H:10]1[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]1[OH:8]

Participants

4

Reactant 1

HCID 86638444(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol

Product 1

HCID 24853445(1S)-1,5-anhydro-1-[2-hydroxy-5-[4-[4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobutyl]benzyl]-4-methylphenyl]-D-glucitolYield 90.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a methanol solution (1.2 mL) of (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-[4-[(1E)-4-[(2-hydroxy-1,1-dimethylethyl)amino]-4-oxobut-1-en-1-yl]benzyl]-4-methylphenyl]-D-glucitol (120 mg, 0.124 mmol) was added 10% palladium-activated carbon (22 mg), and the mixture was stirred overnight under a hydrogen atmosphere at room temperature. The reaction solution was filtered through celite, and evaporated under reduced pressure to obtain a residue. Thus obtained residue was purified with silica gel column chromatography (chloroform:methanol=20:1 to 5:1) to obtain the title compound (58 mg, 90%) 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. customto obtain a residue
  4. customThus obtained residue was purified with silica gel column chromatography (chloroform:methanol=20:1 to 5:1)

Sources & evidence

ORD record
ord-a91c7f8a66974138828440dbb0c62e21
Source dataset
uspto-grants-2011_07
Patent number
US07973012B2

Reaction notes

Loading…