Tetrabutylammonium Fluoride → HCID 57046132, compound

HRID 2396240Notes

Reaction equation

HRID 2396240 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:29])[C:21]([CH2:26][O:27][CH3:28])([CH2:23][O:24][CH3:25])[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:47])[C@@H:15]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si](C(C)(C)C)(C)C)[CH2:33]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:29])[C:21]([CH2:26][O:27][CH3:28])([CH2:23][O:24][CH3:25])[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:47])[C@@H:15]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([OH:39])[CH2:33]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67730928HCID 67730928, compound

Product 1

HCID 57046132HCID 57046132, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 200 mg of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-(2,2-bis[methoxymethyl]propionyloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 160, above] and 4.0 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 105 mg of the title compound as colorless needle-like crystals, melting at between 122° and 123° C.

Sources & evidence

ORD record
ord-1f3285fcf88e4b08855017814fe69534
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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