Acetic Acid → HCID 70360326, compound

HRID 1073456Notes

Reaction equation

HRID 1073456 reaction equation
C([O:4][CH2:5][C@H:6]1[O:26][C@H:25]([C@@H:27]([CH2:36][O:37]C(=O)C)[O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@@H:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:7]1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)C.[O-]CC.[Na+].C(O)(=O)C>C(O)C>[C:10]1([CH2:9][O:8][C@H:7]2[C@H:16]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C@@H:25]([C@@H:27]([CH2:36][OH:37])[O:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[O:26][C@@H:6]2[CH2:5][OH:4])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2723922Sodium ethoxideHCID 70360539HCID 70360539, compound

Product 1

HCID 70360326HCID 70360326, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 485 mg of 2,5-anhydro-3,4,6-tris-O-(phenylmethyl)-D-glycero-D-manno-heptitol 1,7-diacetate in 2 ml of ethanol was treated with 183 μl of an ethanolic solution of sodium ethoxide (2.4N). After 1 hour, 150 μl of glacial acetic acid was added and the mixture evaporated. The residue was taken up in ether, washed with saturated aqueous sodium bicarbonate and brine, dried and evaporated. Flash chromatography, eluting with hexane:ethyl acetate (1:1), gave 290 mg of the desired compound.

Workup

  1. customthe mixture evaporated
  2. washwashed with saturated aqueous sodium bicarbonate and brine
  3. customdried
  4. customevaporated
  5. washFlash chromatography, eluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-c4018497c8614b3a9cc1444da99b737d
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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