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

HRID 628935Notes

Reaction equation

HRID 628935 reaction equation
COP([CH2:7][C:8](=[O:22])[CH:9]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:10][CH2:11][CH2:12][CH3:13])(=O)OC.[Si](OC(CCC)CC(=O)/C=[CH:35]/[C@H:36]1[C@H:40]([O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)[CH2:39][C@@H:38]([Cl:48])[C@@H:37]1[CH2:49][CH2:50][CH2:51][C:52]1[S:56][C:55]([C:57]([O:59][CH3:60])=[O:58])=[CH:54][CH:53]=1)(C(C)(C)C)(C)C>>[Si:15]([O:14][CH:9]([CH2:10][CH2:11][CH2:12][CH3:13])[C:8](=[O:22])/[CH:7]=[CH:35]/[C@H:36]1[C@H:40]([O:41][CH:42]2[CH2:47][CH2:46][CH2:45][CH2:44][O:43]2)[CH2:39][C@@H:38]([Cl:48])[C@@H:37]1[CH2:49][CH2:50][CH2:51][C:52]1[S:56][C:55]([C:57]([O:59][CH3:60])=[O:58])=[CH:54][CH:53]=1)([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17]

Participants

3

Reactant 2

HCID 131735359Dimethyl(3-((tert-butyldimethylsilyl)oxy)-2-oxoheptyl)phosphonateHCID 131735361Methyl 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

Product 1

HCID 131735360Methyl 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-carboxylateYield 86%

Procedure

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).

Sources & evidence

ORD record
ord-e3e8fb5732f74e46ace56968a7255bdd
Source dataset
uspto-grants-2016_04
Patent number
US09315486B2

Reaction notes

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