2,4,6-Trimethylpyridine → HCID 86729321, compound

HRID 1474620Notes

Reaction equation

CC1C=CC(S([O:11][CH2:12][C@@H:13]2[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@@H:16]([OH:21])[C@@:15]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH:40]=[CH2:41])=[CH:34][CH:33]=4)[CH:25]=3)([O:22][CH3:23])[O:14]2)(=O)=O)=CC=1.N1C(C)=CC(C)=CC=1C>CS(C)=O>[CH2:39]([O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:26]2[CH:25]=[C:24]([C@:15]3([O:22][CH3:23])[O:14][C@H:13]([CH:12]=[O:11])[C@@H:18]([OH:19])[C@H:17]([OH:20])[C@H:16]3[OH:21])[CH:29]=[CH:28][C:27]=2[Cl:30])=[CH:33][CH:34]=1)[CH:40]=[CH2:41]

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of ((2R,3S,4S,5R,6S)-6-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl 4-methylbenzenesulfonate (4.5 g, 7.49 mmol) in dry DMSO (30 mL), was added collidine (6.95 mL, 52.44 mmol) and the mixture was heated at 150° C. for 45 min. After the completion of the reaction as monitored by TLC, the reaction mixture was used as such for the next step.

Workup

customAfter the completion of the reaction

Sources & evidence

ORD record: ord-24393ba946704ccfb7cdd4f462ad31ff
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018249B2

Reaction notes

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