Dichloromethane → 1-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-beta-D-ribofuranoside

HRID 965194Notes

Reaction equation

HRID 965194 reaction equation
[Si:1]([CH:18]([OH:28])[C@H:19]1[O:25][C@@H:22]([O:23][CH3:24])[C@H:21]([OH:26])[C@@H:20]1[OH:27])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(Cl)Cl>C(Cl)Cl.N1C=CC=CC=1>[Si:1]([CH:18]([OH:28])[C@H:19]1[O:25][C@@H:22]([O:23][CH3:24])[C@:21]([C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([OH:26])[C@:20]1([C:29](=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[OH:27])([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 7412Benzoyl chlorideHCID 186611941-O-methyl 5-(t-butyldiphenylsilyl)-beta-D-ribofuranoside

Product 1

HCID 186611931-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-beta-D-ribofuranoside

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1-O-methyl 5-(t-butyldiphenylsilyl)-β-D-ribofuranoside (579 mg, 1.44 mmol) in methylene chloride-pyridine (4:1, 12.5 ml) was added dropwise benzoyl chloride (0.367 ml, 3.16 mmol) at 0° C. The reaction mixture was stirred for 2.5 h at 0° C. and for 14.5 h at room temperature. Ice was added to quench the reaction and the mixture was stirred for 1 h. Methylene chloride (100 ml) was added and two phases were separated. Organic layer was washed with water, saturated ammonium chloride, and brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness to yield 1-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-β-D-ribofuranoside in crude form, which was then purified by silica gel column chromatography (Hx-EtOAc, 5:1→1:1) to yield 1-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-β-D-ribofuranoside in more pure form [Rf =0.75 (CHCl3 --MeOH, 10:1), 869 mg, 99%] as a thick syrup. 1H NMR (CDCl3) d 1.05 (s, 9H, t-Bu), 3.42 (s, 3H, --OCH3), 3.86 (dd, J=11.1 and 4.8 Hz, 1H, H-5a), 3.92 (dd, J=11.1 and 4.7 Hz, 1H, H-5b), 4.48 (dd, J=10.6 and 4.6 Hz, 1H), 5.15 (s, 1H), 5.63 (d, J=5.0 Hz, 1H), 5.82 (pseudo t, J=5.8 and 5.4 Hz, 1H), 7,29-8.18 (m, 20H, Ar). Anal. Calcd for C36H38O7Si1 : C, 70.79; H, 6.27; Found: C, 71.01; H, 6.20.

Workup

  1. additionIce was added
  2. customto quench
  3. customthe reaction
  4. stirringthe mixture was stirred for 1 h
  5. customtwo phases were separated
  6. washOrganic layer was washed with water, saturated ammonium chloride, and brine
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-7da9227dcbf6454bbcd7445ed898f237
Source dataset
uspto-grants-1998_06
Patent number
US05773423

Reaction notes

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