Acetic Acid → [(2R,3R,4R,5S)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol

HRID 1073454Notes

Reaction equation

HRID 1073454 reaction equation
[C:1]1([CH2:7][O:8][C@H:9]2[C@H:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:33]([CH2:43][O:44]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[O:32][C@H:10]2[CH2:11][O:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C>CC(C)=O>[C:1]1([CH2:7][O:8][C@H:9]2[C@H:34]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C@@H:33]([CH2:43][OH:44])[O:32][C@H:10]2[CH2:11][OH:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 70360554HCID 70360554, compound

Product 1

HCID 11210109[(2R,3R,4R,5S)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanolYield 73.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 847 mg of 2,5-anhydro-3,4-bis-O-(phenylmethyl)-1,6-bis-O-(triphenylmethyl)-D-glucitol in 5 ml of acetone was treated with 16 ml of 80% aqueous acetic acid with stirring for 1 hour at 80° C., for 20 hours at room temperature and then evaporated in vacuo. The residue was taken up in ether, washed with brine, dried and evaporated to an oil. Chromatography of the oil, eluting with ether, gave 260 mg of the desired compound.

Workup

  1. customevaporated in vacuo
  2. washwashed with brine
  3. customdried
  4. customevaporated to an oil
  5. washChromatography of the oil, eluting with ether

Sources & evidence

ORD record
ord-49d0500de96441aaa73240968b2a51b2
Source dataset
uspto-grants-1990_11
Patent number
US04968790

Reaction notes

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