HCID 86621844, compound → HCID 86621846, compound

HRID 1713584Notes

Reaction equation

HRID 1713584 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C@@:14]2([O:53][CH3:54])[C@H:19]([O:20]CC3C=CC=CC=3)[C@@H:18]([O:28]CC3C=CC=CC=3)[C@H:17]([O:36]CC3C=CC=CC=3)[C@@H:16]([CH2:44][O:45]CC3C=CC=CC=3)[O:15]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][CH2:12][CH2:13][C@@:14]2([O:53][CH3:54])[C@H:19]([OH:20])[C@@H:18]([OH:28])[C@H:17]([OH:36])[C@@H:16]([CH2:44][OH:45])[O:15]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 86621844HCID 86621844, compound

Product 1

HCID 86621846HCID 86621846, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-((2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2H-pyran-2-yl)ethyl 4-methylbenzenesulfonate (9) (0.32 g, 0.42 mmol) was dissolved in MeOH (3 mL). Pd/C (60 mg, 10% Pd/C) was added and the reaction flask was flushed with H2 (3×), and then allowed to stir under a balloon of H2. After 15 h, the reaction was filtered through a celite plug, rinsing with MeOH and CH2Cl2 and concentrated to provide an oil (165 mg, 100%). LC/MS: tR=1.36 min, calcd for C16H24O9S: 392.11, found 415.2 (M+Na)+.

Workup

  1. customthe reaction flask was flushed with H2 (3×)
  2. filtrationthe reaction was filtered through a celite plug
  3. washrinsing with MeOH and CH2Cl2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-161cc1ffffba49f484e9f0107c95f9c5
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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