Tetrahydrofuran → 1-O-methyl 2,3-dibenzoyl-beta-D-ribofuranoside

HRID 965195Notes

Reaction equation

[Si]([CH:18]([OH:44])[C@H:19]1[O:25][C@@H:22]([O:23][CH3:24])[C@:21]([C:27](=[O:34])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([OH:26])[C@:20]1([C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[OH:35])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>>[C:27]([C@@:21]1([OH:26])[C@:20]([C:36](=[O:43])[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([OH:35])[C@@H:19]([CH2:18][OH:44])[O:25][C@H:22]1[O:23][CH3:24])(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Reactant 3

HCID 8028Tetrahydrofuran

HCID 2724141Tetrabutylammonium Fluoride

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

Product 1

HCID 186611921-O-methyl 2,3-dibenzoyl-beta-D-ribofuranosideYield 89.1%

Procedure

A solution of 1-O-methyl 5-(t-butyldiphenylsilyl)-2,3-dibenzoyl-β-D-ribofuranoside (849 mg, 1.39 mmol) and 1.0M tetrabutylammonium fluoride in THF (1.53 ml, 1.53 mmol) was stirred for 2 h at room temperature. After evaporation of the solvent, the residue was purified by silica gel column chromatography (Hx-EtOAc, 1:1) to yield 1-O-methyl 2,3-dibenzoyl-β-D-ribofuranoside [Rf =0.50 (Hx-EtOAc, 1:1), 461 mg, 89%] as thick syrup. 1H NMR (DMSO-d6) d 3.38 (s, 3H, --OCH3), 3.62 (m, 2H, H-5), 4.37 (q, J=5.2 Hz, 1H, H-4), 5.02 (pseudo t, J=6.0 and 5.3 Hz, 1H, exchangeable with D2O, 5-OH), 5.18 (s, 1H, H-1), 5.45 (m, 1H, H-2), 5.53 (t, J=5.2 Hz, 1H, H-3), 7.42-7.88 (m, 10H, Ar). Anal. Calcd for C20 H20O7 : C, 64.51; H, 5.41; Found: C, 64.37; H, 5.47.

Workup

customAfter evaporation of the solvent
customthe residue was purified by silica gel column chromatography (Hx-EtOAc, 1:1)

Sources & evidence

ORD record: ord-9ba99f51bf674f22b524b15a8e61455d
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05773423

Reaction notes

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