Tetrabutylammonium Fluoride → HCID 53864570, compound

HRID 2396245Notes

Reaction equation

HRID 2396245 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:20](=[O:32])[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:23])[CH3:22])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:50])[C@@H:15]2[CH2:33][CH2:34][C@H:35]2[O:40][C:39](=[O:41])[CH2:38][C@H:37]([O:42][Si](C(C)(C)C)(C)C)[CH2:36]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:32])[C:21]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([CH3:22])[CH3:23])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:50])[C@@H:15]2[CH2:33][CH2:34][C@H:35]2[O:40][C:39](=[O:41])[CH2:38][C@H:37]([OH:42])[CH2:36]2)=[CH:10]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 54208033HCID 54208033, compound

Product 1

HCID 53864570HCID 53864570, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Example 2, above, was followed, but using 419 mg of (4R,6R)-6-{(1S,2S,6S,8S,8aR)-2-[1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-(2-benzyloxy-2-methylpropionyloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example 169, above] and 8.1 ml of a 1.0 molar solution of tetrabutylammonium fluoride in tetrahydrofuran, to give 263 mg of the title compound as a colorless foam.

Sources & evidence

ORD record
ord-81e37424da7c463daab51f662e5a29f6
Source dataset
uspto-grants-1996_02
Patent number
US05491167

Reaction notes

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