Reaktion #10232

ord-b8e538f0579c41db942698431874f3f6

Reaktionsgleichung

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

Edukte

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

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

93.1%; (5S)-6-benzoyloxy-3,5-dihydroxyhexanoic tert-butyl ester: 3.4%; (2S,4R)-4-hydroxy-6-oxo-2-[(benzoyloxy)methyl]tetrahydro-2H-pyran: 0.1%; 2-[(4R,6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic methyl ester: 0.1%.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094594B2uspto-grants-2006_08