2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose → (3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-one

HRID 1713577Notes

Reaction equation

HRID 1713577 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>CS(C)=O.CC(OC(C)=O)=O.CCOC(C)=O>[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:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[O:11][C:10]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 109405022,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucopyranose

Product 1

HCID 10907626(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-((benzyloxy)methyl)oxan-2-oneYield 95%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 7918Acetic AnhydrideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-ol (4) (2.00 g, 3.7 mmol, Senn Chemicals) was dissolved in solution of 12.0 mL DMSO and 8.0 mL Ac2O. After stirring for 12 h, the reaction was diluted with EtOAc, washed with H2O (1×), sat. NaHCO3 (1×), then dried (Na2SO4) and concentrated using high-vacuum to provide a syrup (1.89 g, 95%). LC/MS 100% (ELSD) tR=3.10 min, calcd for C34H34O6: 538.24, found 539.4 (M+H)+.

Workup

  1. washwashed with H2O (1×), sat. NaHCO3 (1×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-26fafb295e9543acba3bb4dd4a9ba6fc
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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