2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → 1,3,4,5-Tetra-O-benzyl-D-glucitol

HRID 1747012Notes

Reaction equation

HRID 1747012 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][CH:10]1[OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([O:8][C@H:9]([C@@H:14]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C@H:13]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:12]([OH:11])[CH2:31][O:32][CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[CH2:10][OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranoseHCID 21226445Aluminium lithium hydride

Product 1

HCID 108752501,3,4,5-Tetra-O-benzyl-D-glucitolYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-[(benzyloxy)methyl]oxan-2-ol 1 (25 g, 46.24 mmol) in THF (310 mL) was added solid LiAlH4 (6.14 g, 161.84 mmol) portion-wise at 0° C. and the reaction mixture was stirred at room temperature for 20 h. The reaction mixture was cooled to 0° C. and carefully quenched with with saturated Na2SO4 solution (35 mL) and the reaction mixture was stirred at room temperature for 30 min. Solid was filtered through a celite pad and the filtrate was diluted with ethyl acetate (250 mL). Organic part was separated and washed with saturated aqueous solution of NH4Cl (3×100 mL). The organic phase was dried over Na2SO4, concentrated under reduced pressure to get crude was purified by column chromatography using 100-200 mesh silica gel and eluting with 12% EtOAc/hexane to get (2S,3R,4R,5R)-2,3,4,6-tetrakis(benzyloxy)hexane-1,5-diol 2 (24 g, 95%) as sticky oil.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customcarefully quenched with with saturated Na2SO4 solution (35 mL)
  3. stirringthe reaction mixture was stirred at room temperature for 30 min
  4. filtrationSolid was filtered through a celite pad
  5. additionthe filtrate was diluted with ethyl acetate (250 mL)
  6. customOrganic part was separated
  7. washwashed with saturated aqueous solution of NH4Cl (3×100 mL)
  8. dry with materialThe organic phase was dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto get crude
  11. customwas purified by column chromatography
  12. washeluting with 12% EtOAc/hexane

Sources & evidence

ORD record
ord-aa6660dc54e24656996153179b044edc
Source dataset
uspto-grants-2015_10
Patent number
US09150557B1

Reaction notes

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