Methanol → HCID 70360277, compound

HRID 1073455Notes

Reaction equation

HRID 1073455 reaction equation
[C:1]1([CH2:7][O:8][CH2:9][C@H:10]2[O:30][C@H:29]([C@@H:31]([CH2:33][OH:34])[OH:32])[C@@H:20]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:11]2[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:37](Br)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.CO>CN(C)C=O>[C:1]1([CH2:7][O:8][CH2:9][C@H:10]2[O:30][C@H:29]([C@@H:31]([CH2:33][O:34][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[O:32][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C@@H:20]([O:21][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@@H:11]2[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 70360287HCID 70360287, compound

Product 1

HCID 70360277HCID 70360277, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

An 850 mg portion of 2,5-anhydro-1,3,4-tris-O-(phenylmethyl)-D-glycero-D-manno-heptitol was dissolved in dry dimethylformamide and added to a slurry of 218 mg of sodium hydride in dimethylformamide. After stirring 1 hour, 1.9 ml of benzyl bromide was added, the mixture stirred overnight, 5 ml to methanol added and the solvents evaporated. The residue was taken up in 50 ml of water and 50 ml of dichloromethane, the organic layer separated, washed with water and brine, dried and evaporated to an orange oil. This oil was flash chromatographed, eluting with hexane:ether (5:1). Evaporation of the fractions gave 1.06 g of the desired compound.

Workup

  1. stirringthe mixture stirred overnight
  2. customthe solvents evaporated
  3. custom50 ml of dichloromethane, the organic layer separated
  4. washwashed with water and brine
  5. customdried
  6. customevaporated to an orange oil
  7. customchromatographed
  8. washeluting with hexane:ether (5:1)
  9. customEvaporation of the fractions

Sources & evidence

ORD record
ord-342b09a419e8461a81ff2632a7eee624
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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