2,3,5-Tri-O-benzoyl-2-C-methyl-betaD-ribofuranose → 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose

HRID 1818445Notes

Reaction equation

HRID 1818445 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:17]([O:25][C@:26]1([CH3:51])[C@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:30]([CH2:41][O:42][C:43](=[O:50])[C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[O:29][C@H:27]1[OH:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.COCCOC>[C:1]([O:28][C@@H:27]1[O:29][C@H:30]([CH2:41][O:42][C:43](=[O:50])[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[C@@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@:26]1([CH3:51])[O:25][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O:25][C@:26]1([CH3:51])[C@H:31]([O:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C@@H:30]([CH2:41][O:42][C:43](=[O:50])[C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[O:29][C@H:27]1[OH:28])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 108852622,3,5-Tri-O-benzoyl-2-C-methyl-betaD-ribofuranoseHCID 20571369benzoyl chloride TEA

Product 2

HCID 108755601,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranoseHCID 108852622,3,5-Tri-O-benzoyl-2-C-methyl-betaD-ribofuranose

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

One preferred embodiment of the present invention is exemplified in FIG. 1 and comprises reacting D-fructose in the presence of CaO/water at 23-40° C. for 6-22 hours, and then adding CO2 and oxalic acid to the reaction mixture and allowing the reaction to proceed for 8-12 hours to form 2-C-methyl-D-ribonic-γ-lactone (1); reacting 2-C-methyl-D-ribonic-γ-lactone (1) with 4-dimethylaminopyridine (DMAP) and triethylamine (TEA) in 1,2-dimethoxyethane (DME) at temperature of from about 5° C. to 25° C. for about 30 minutes, and then cooling the mixture to about 5° C. and adding benzoyl chloride to provide 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribonic-γ-lactone (2); reacting 2,3,5-tri-O-benzoyl-2-C-methyl-D-ribonic-γ-lactone (2) with Red-Al/ethanol in toluene at a temperature of from about −5 to 0° C. for about 40 minutes to provide 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose (3); and finally adding benzoyl chloride/TEA to a cold solution of 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose (3) in the presence of DMAP and DME and allowing the reaction to proceed for from about 4 hours to about 12 hours at a temperature of from about 5 to about 50° C., thereby providing the final product (4), 2,3,5-tri-O-benzoyl-2-C-methyl-β-D-ribofuranose.

Workup

  1. customthe reaction
  2. customto proceed for from about 4 hours to about 12 hours at a temperature of from about 5 to about 50° C.

Sources & evidence

ORD record
ord-6bdf2f2ed18b4fc7a80b6d0a80514689
Source dataset
uspto-grants-2009_10
Patent number
US07598373B2

Reaction notes

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