beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate → Ribofuranose, 1-acetate 2,3,5-tribenzoate

HRID 968506Notes

Reaction equation

HRID 968506 reaction equation
[C:1]([O:4][C@@H:5]1[O:27][C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]>C(O)C>[C:1]([O:4][C@H:5]1[O:27][C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=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:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 81455beta-D-Ribofuranose, 1-acetate 2,3,5-tribenzoate

Product 1

HCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

mp 129-130° C. (EtOH 95) (lit.(1) mp 130-131° C.) 1H NMR (200 MHz, CDCl3): δ 8.09-7.87 (m, 6H, HArom), 7.62-7.31 (m, 9H, H Arom) 6.43 (s, 1H, H1), 5.91 (dd, 1H, H3, J3,4 6.7 Hz; J3,2 4.9 Hz), 5.79 (pd, 1H, H2, J2,3 4,9 Hz; J1,2<1), 4.78 (m, 2H, H4 and H5), 4.51 (dd, 1H, H5, J5,5′13,1 Hz, J5′,4 5,5 Hz), 2.00 (s, 3H CH3CO); (identical to commercial 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose) Mass analysis (FAB+, GT) m/z 445 (M−OAc)+Elemental analysis C28H24O9 Calculated C, 66.66 H, 4.79. found C, H.

Sources & evidence

ORD record
ord-928dbdfe3d184d399558fb4e369242dc
Source dataset
uspto-grants-2007_12
Patent number
US07304043B2

Reaction notes

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