Water → HCID 11016258, compound

HRID 843212Notes

Reaction equation

HRID 843212 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:16]([CH2:17][OH:18])[C@@H:15]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:14]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.OP(O)(O)=O.O>CS(C)=O>[CH2:1]([O:8][C@@H:9]1[C@@H:16]([CH:17]=[O:18])[C@@H:15]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C@@H:14]([CH2:27][O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:13][C@@H:10]1[O:11][CH3:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1004Phosphoric AcidHCID 10868DicyclohexylcarbodiimideHCID 15929787HCID 15929787, compound

Product 1

HCID 11016258HCID 11016258, compoundYield 95.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of methyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-(hydroxymethyl)-α-D-galacto-hexopyranoside (5.13 g, 10.72 mmol) in 25 ml of dry DMSO, 5.0 g of DCC and 0.5 ml H3PO4 were added. The mixture was stirred overnight at room temperature. The reaction mixture was treated with water (100 ml), and extracted several times with ethyl acetate. The combined organic extracts were washed with a saturated sodium hydrogen carbonate solution, dried with MgSO4 and concentrated in vacua. Purification of the crude product by flash chromatography with petroleum ether/ethyl acetate (4:1) gave 4.9 g (94%) methyl 2,4,6-tri-O-benzyl-3-deoxy-3-C-(formyl)-α-D-galacto-hexopyranoside as a colorless oil. —TLC (petroleum ether/ethyl acetate, 4:1): Rf=0.36.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic extracts were washed with a saturated sodium hydrogen carbonate solution
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacua
  5. customPurification of the crude product by flash chromatography with petroleum ether/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-a3796d2fc1c54319bceb570c0f052722
Source dataset
uspto-grants-2002_04
Patent number
US06376662B1

Reaction notes

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