Triphenylphosphine → HCID 66969084, compound

HRID 1359926Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([C:15]1[CH:53]=[CH:52][C:18]([CH2:19][C:20]2[C:21]([CH3:51])=[C:22]([OH:50])[CH:23]=[C:24]([C:26]3([O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]3[O:29][C:30](=[O:32])[CH3:31])[OH:27])[CH:25]=2)=[CH:17][CH:16]=1)[CH3:14].[CH:54]1(O)[CH2:57][CH2:56][CH2:55]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH:54]1([O:50][C:22]2[CH:23]=[C:24]([C:26]3([O:44][C@H:43]([CH2:45][O:46][C:47](=[O:49])[CH3:48])[C@@H:38]([O:39][C:40](=[O:42])[CH3:41])[C@H:33]([O:34][C:35](=[O:37])[CH3:36])[C@H:28]3[O:29][C:30](=[O:32])[CH3:31])[OH:27])[CH:25]=[C:20]([CH2:19][C:18]3[CH:17]=[CH:16][C:15]([CH2:13][CH3:14])=[CH:53][CH:52]=3)[C:21]=2[CH3:51])[CH2:57][CH2:56][CH2:55]1

Participants

Conditions

Temperature: 70 °C

Procedure

Diethyl azodicarboxylate (0.38 g) dissolved in THF (0.5 mL) is added to 3-(4-ethylbenzyl)-1-hydroxy-2-methyl-5-(2,3,4,6-tetra-O-acetyl-D-glucopyranos-1-yl)-benzene (0.27 g), cyclobutanol (0.1 mL) and triphenylphosphine (0.56 g) dissolved in THF (2 mL). The mixture is heated with stirring at 70° C. overnight. After cooling to room temperature, the solvent is evaporated and the residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel.

Workup

temperatureThe mixture is heated
temperatureAfter cooling to room temperature
customthe solvent is evaporated
customthe residue is purified by chromatography (cyclohexane/ethyl acetate 4:1->1:3) on silica gel

Sources & evidence

ORD record: ord-2f17205d54424b77ae3d4485f77e18ff
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879807B2

Reaction notes

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