Sulfuric Acid → HCID 118108846, compound

HRID 1508643Notes

Reaction equation

HRID 1508643 reaction equation
S(=O)(=O)(O)O.[CH2:6]([O:13][C@:14]1([CH3:38])[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:17]([CH2:27][O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[O:16][C@@H:15]1[O:36]C)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(OCC)(=O)C>C(O)(=O)C.O>[CH2:6]([O:13][C@:14]1([CH3:38])[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:17]([CH2:27][O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[O:16][C@@H:15]1[OH:36])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 118108881Methyl 2-C-methyl-2,3,5-tris-O-(phenylmethyl)-α-D-ribofuranoside

Product 1

HCID 118108846HCID 118108846, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

4.9 g of concentrated sulfuric acid was added dropwise to a solution of 9.0 g of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-2-methoxy-3-methyloxolane in 80 mL of acetic acid and 20 mL of water at room temperature, and the obtained mixture was then stirred at 70° C. for 3 hours. Thereafter, the reaction mixture was cooled to 30° C., and 200 mL of water and 200 mL of ethyl acetate were then added to the mixture. The organic layer was fractionated, and it was successively washed with 200 mL of 1 mol/L hydrochloric acid and 200 mL of a saturated sodium chloride aqueous solution. The solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel column chromatography, so as to obtain 5.5 g of (2S,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-3-methyloxolan-2-ol in the form of a colorless oily product.

Workup

  1. temperatureThereafter, the reaction mixture was cooled to 30° C.
  2. washit was successively washed with 200 mL of 1 mol/L hydrochloric acid and 200 mL of a saturated sodium chloride aqueous solution
  3. distillationThe solvent was distilled away under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0164d28999be4c76ab212eb1d155762e
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

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