α-D-Mannose pentaacetate → HCID 57413590, compound

HRID 1428972Notes

Reaction equation

[C:1]([O:4][C@H:5]1[O:22][C@H:21]([CH2:23][O:24]C(=O)C)[C@@H:16]([O:17]C(=O)C)[C@H:11]([O:12]C(=O)C)[C@@H:6]1[O:7]C(=O)C)(=O)[CH3:2].OC1C=[CH:31][C:32]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([O:47][CH3:48])=[O:46])[CH:40]=2)=[C:33]([CH:38]=1)[C:34]([O:36][CH3:37])=[O:35]>>[CH3:48][O:47][C:45]([C:41]1[CH:40]=[C:39]([C:32]2[CH:31]=[CH:2][C:1]([O:4][C@@H:5]3[C@@H:6]([OH:7])[C@@H:11]([OH:12])[C@H:16]([OH:17])[C@@H:21]([CH2:23][OH:24])[O:22]3)=[CH:38][C:33]=2[C:34]([O:36][CH3:37])=[O:35])[CH:44]=[CH:43][CH:42]=1)=[O:46]

Participants

Reactant 2

HCID 11741089α-D-Mannose pentaacetate

HCID 57413866HCID 57413866, compound

Product 1

HCID 57413590HCID 57413590, compoundYield 73%

Procedure

6 was prepared via glycosidation between α-D-mannose pentaacetate and methyl 5-hydroxy-2-(3-methoxycarbonylphenyl)benzoate following the procedure previously described.25 Yield: 73%. 1H NMR (300 MHz, METHANOL-d4) δ ppm 3.56-3.68 (m, 4H) 3.68-3.84 (m, 3H) 3.86-3.98 (m, 4H) 4.06 (dd, J=3.30, 1.92 Hz, 1H) 5.60 (d, J=1.92 Hz, 1H) 7.29-7.43 (m, 2H) 7.45-7.53 (m, 2H) 7.56 (d, J=2.47 Hz, 1H) 7.84-7.92 (m, 1H) 7.93-8.04 (m, 1H). MS (ESI): found [M+H]+, 449.0.

Sources & evidence

ORD record: ord-203823f0838d43de805064b653a3339c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937167B2

Reaction notes

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