Sodium Acetate → 2-(4-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanol

HRID 425063Notes

Reaction equation

HRID 425063 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[CH:59]=[CH:58][C:10]([CH2:11][C:12]2[CH:13]=[C:14]([C@H:19]3[C@H:24]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@@H:23]([O:33][CH2:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C@H:22]([O:41][CH2:42][C:43]4[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=4)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]4[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=4)[O:20]3)[CH:15]=[CH:16][C:17]=2[Cl:18])=[CH:9][CH:8]=1)C=C.C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd](Cl)Cl>[Cl:18][C:17]1[CH:16]=[CH:15][C:14]([C@H:19]2[C@H:24]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C@@H:23]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:22]([O:41][CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C@@H:21]([CH2:49][O:50][CH2:51][C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=3)[O:20]2)=[CH:13][C:12]=1[CH2:11][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][CH2:5][OH:4])=[CH:59][CH:58]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 57684691HCID 57684691, compound

Product 1

HCID 576846952-(4-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanolYield 42%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

(2S,3S,4R,5R,6R)-2-(3-(4-(2-(allyloxy)ethyl)benzyl)-4-chlorophenyl)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran (intermediate BK) (50 mg, 0.061 mmol) was taken up in 90% aqueous acetic acid (1 mL), and sodium acetate (30.4 mg, 0.37 mmol) was added, followed by palladium(II)chloride (27.4 mg, 0.154 mmol). The mixture was heated at 70° C. for 5 h. Solvent was evaporated and the residue was taken up in 2 mL DCM and the mixture was filtered through a short Celite® pad. The pad was washed with a copious amount of DCM until all material had eluted. After evaporation of solvent, the residue was purified by TLC using 4:1 hexane:EtOAc to obtain intermediate BL (20 mg, yield 42%). LC-ESI-MS (m/z): 770 (M+H), 791 (M+H+Na).

Workup

  1. customSolvent was evaporated
  2. filtrationthe mixture was filtered through a short Celite® pad
  3. washThe pad was washed with a copious amount of DCM until all material
  4. washhad eluted
  5. customAfter evaporation of solvent
  6. customthe residue was purified by TLC
  7. customEtOAc to obtain intermediate BL (20 mg, yield 42%)

Sources & evidence

ORD record
ord-a2d87e7edea64bb69dabf786b6924ae9
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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