Tetrabutylammonium Fluoride → HCID 15341225, compound

HRID 2396219Notes

Reaction equation

HRID 2396219 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:30])[CH:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:48])[C@@H:15]2[CH2:31][CH2:32][C@H:33]2[O:38][C:37](=[O:39])[CH2:36][C@H:35]([O:40][Si](C(C)(C)C)(C)C)[CH2:34]2)=[CH:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:30])[CH:21]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:48])[C@@H:15]2[CH2:31][CH2:32][C@H:33]2[O:38][C:37](=[O:39])[CH2:36][C@H:35]([OH:40])[CH2:34]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 15341224HCID 15341224, compound

Product 1

HCID 15341225HCID 15341225, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 800 mg of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-[(2RS)-2-phenoxypropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example127, above] and 24.7 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 324 mg of the title compound as a white powder.

Sources & evidence

ORD record
ord-786349a39cf54a6fa03c204734e03f67
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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