Tetrabutylammonium Fluoride → HCID 54361726, compound

HRID 2396237Notes

Reaction equation

HRID 2396237 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:28])[C:21]([CH2:26][CH3:27])([O:24][CH3:25])[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:46])[C@@H:15]2[CH2:29][CH2:30][C@H:31]2[O:36][C:35](=[O:37])[CH2:34][C@H:33]([O:38][Si](C(C)(C)C)(C)C)[CH2:32]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:28])[C:21]([CH2:26][CH3:27])([O:24][CH3:25])[CH2:22][CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:46])[C@@H:15]2[CH2:29][CH2:30][C@H:31]2[O:36][C:35](=[O:37])[CH2:34][C@H:33]([OH:38])[CH2:32]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53996491HCID 53996491, compound

Product 1

HCID 54361726HCID 54361726, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 548 mg of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-(2-ethyl-2-methoxybutyryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsiloxy-2H-pyran-2-one [prepared as described in Example 154, above] and 11.3 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 288 mg of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-e9cb87794e5c435eb9196f3219424647
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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