Acetic Acid → 1-o-Acetyl-2,3,5-tri-o-benzoyl-l-ribose

HRID 1944797Notes

Reaction equation

HRID 1944797 reaction equation
[C:1]([O:9][C@H:10]1[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH2:26][O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:14][CH:11]1OC)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=C[C@H]([C@H]([C@H](CO)O)O)O.C(OC(=O)C)(=O)C.[C:53]([OH:56])(=[O:55])[CH3:54].S(=O)(=O)(O)O>O>[C:53]([O:56][CH:11]1[O:14][C@@H:15]([CH2:26][O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:10]1[O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:55])[CH3:54]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 90428L-RiboseHCID 110162552,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose

Product 1

HCID 126715131-o-Acetyl-2,3,5-tri-o-benzoyl-l-ribose

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.37 g of crude 2,3,5-tri-O-benzoyl-1-O-methyl-L-ribofuranose synthesized from L-ribose (1.0 g; 6.66 mmol) in accordance with the method described in Helvetica Chimica Acta 1959, (121), 1171-1173p was added to a 100-ml flask. Thereafter, acetic anhydride (3.73 ml; 5.95 equivalents) and acetic acid (1.60 ml; 2.80 equivalents) were added thereto. The obtained mixture was cooled on ice, and thereafter, concentrated sulfuric acid (530 μl; 1.5 equivalents) was slowly added dropwise thereto. After completion of the reaction for 30 minutes, cold water (50 ml) was slowly added dropwise to the reaction solution, and an upper aqueous layer was separated. The precipitated semi-oily solid was dried under reduced pressure. Thus, 3.97 g of crude 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose was obtained in the form of a light yellow oily solid. The obtained solid was analyzed by HPLC. As a result, the ratio of α-/β-anomers in the crude 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose was 35/65, and the reaction yield of the β-anomer from the total 3 steps was 56%.

Workup

  1. additionwas added to a 100-ml flask
  2. temperatureThe obtained mixture was cooled on ice
  3. customAfter completion of the reaction for 30 minutes
  4. customan upper aqueous layer was separated
  5. customThe precipitated semi-oily solid
  6. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-bf01cb89f005484e89f3ecd7dddf15ea
Source dataset
uspto-grants-2013_03
Patent number
US08394935B2

Reaction notes

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