تفاعل #716117

ord-e3e8fb5732f74e46ace56968a7255bdd

معادلة التفاعل

CCCCC(O[Si](C)(C)C(C)(C)C)C(=O)CP(=O)(OC)OC

dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate

Dimethyl(3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate

CCCC(CC(=O)/C=C/[C@@H]1[C@@H](CCCc2ccc(C(=O)OC)s2)[C@H](Cl)C[C@H]1OC1CCCCO1)O[Si](C)(C)C(C)(C)C

compound 11

Methyl 5-(3-((1R,2R,3R,5R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-3-oxooct-1-en-1-yl)-5-chloro-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)propyl)thiophene-2-carboxylate

→

CCCCC(O[Si](C)(C)C(C)(C)C)C(=O)/C=C/[C@@H]1[C@@H](CCCc2ccc(C(=O)OC)s2)[C@H](Cl)C[C@H]1OC1CCCCO1

Compound 15

المردود 86.0%

Methyl 5-(3-((1R,2R,3R,5R)-2-((E)-4-((tert-butyldimethylsilyl)oxy)-3-oxooct-1-en-1-yl)-5-chloro-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)propyl)thiophene-2-carboxylate

المردود 86.0%

المتفاعلات

dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate

Dimethyl(3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate

—

aldehyde

compound 11

Methyl 5-(3-((1R,2R,3R,5R)-2-((E)-5-((tert-butyldimethylsilyl)oxy)-3-oxooct-1-en-1-yl)-5-chloro-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)propyl)thiophene-2-carboxylate

الكواشف

لا شيء

ظروف التفاعل

الظروف التفصيلية

See reaction.notes.procedure_details.

الإجراء التجريبي

Compound 15 (1.32 g) was prepared in 86% yield by employing dimethyl (3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonate 6 and aldehyde 10 according to the procedures described for compound 11 (see Schemes 1 and 2).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09315486B2uspto-grants-2016_04