反応 #10230

ord-0993d93248bf475d918c0a23581a47a7

反応方程式

CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1
(5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester
O=C1C[C@H](O)C[C@@H](COC(=O)c2ccccc2)O1
(2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran
COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1
2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester
→
CC(C)(C)OC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1
2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester

反応物

CC(C)(C)OC(=O)CC(O)C[C@H](O)COC(=O)c1ccccc1
(5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester
O=C1C[C@H](O)C[C@@H](COC(=O)c2ccccc2)O1
(2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran
COC(=O)C[C@H]1C[C@@H](COC(=O)c2ccccc2)OC(C)(C)O1
2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester

試薬

なし

反応条件

詳細条件
See reaction.notes.procedure_details.

実験手順

78.8%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 7.5%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 5.9%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 3.0%.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07094594B2uspto-grants-2006_08