Tetrabutylammonium Fluoride → HCID 67730995, compound

HRID 2396233Notes

Reaction equation

HRID 2396233 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:26])[C:21]([O:24][CH3:25])([CH3:23])[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:44])[C@@H:15]2[CH2:27][CH2:28][C@H:29]2[O:34][C:33](=[O:35])[CH2:32][C@H:31]([O:36][Si](C(C)(C)C)(C)C)[CH2:30]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:26])[C:21]([O:24][CH3:25])([CH3:22])[CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:44])[C@@H:15]2[CH2:27][CH2:28][C@H:29]2[O:34][C:33](=[O:35])[CH2:32][C@H:31]([OH:36])[CH2:30]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67731003HCID 67731003, compound

Product 1

HCID 67730995HCID 67730995, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 814 mg of (4R,6R)-6-([1S,2S,6S,8S,8aR]-2-{1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-(2-methoxy-2-methylpropionyloxy]-2-methyl-1-naphthyl}ethyl)tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 148, above] and 17.5 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 518 mg of the title compound as colorless needle-like crystals, melting at between 150° and 152° C.

Sources & evidence

ORD record
ord-a7b50b26b1a64fdc8923562abe0fabcf
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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