2,2-Diethyl-4-pentenoyl chloride → (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2,2-diethyl-4-pentenoyloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

HRID 400158

반응식

[OH:1][C@@H:2]1[C@H:11]2[C:6]([CH:7]=[CH:8][C@H:9]([CH3:29])[C@@H:10]2[CH2:12][CH2:13][C@H:14]2[O:19][C:18](=[O:20])[CH2:17][C@H:16]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1.[CH2:30]([C:32]([CH2:39][CH3:40])([CH2:36][CH:37]=[CH2:38])[C:33](Cl)=[O:34])[CH3:31]>>[CH2:30]([C:32]([CH2:39][CH3:40])([CH2:36][CH:37]=[CH2:38])[C:33]([O:1][C@@H:2]1[C@H:11]2[C:6]([CH:7]=[CH:8][C@H:9]([CH3:29])[C@@H:10]2[CH2:12][CH2:13][C@H:14]2[O:19][C:18](=[O:20])[CH2:17][C@H:16]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1)=[O:34])[CH3:31]

참가 물질

반응물 2

HCID 189438302,2-Diethyl-4-pentenoyl chloride

HCID 53731106(4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

생성물 1

HCID 22856163(4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2,2-diethyl-4-pentenoyloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one수율 77.5%

실험 절차

A procedure similar to that described in Example 6, above, was followed, but using 1.26 g (3.0 mmol) of (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Japanese Patent Kokai Application No. Sho 59-175450] and 2.09 g (12.2 mmol) of 2,2-diethyl-4-pentenoyl chloride, to provide 1.30 g of the title compound.

출처 및 근거

ORD 기록: ord-5ef09ae887a04cbfa547e2ec296246b6
출처 데이터셋: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05827855

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