HCID 86658276, compound → Benzyl 2,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzoyl-alpha-D-mannopyranoside

HRID 74838Notes

Reaction equation

C([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[O:8][C@H:7]([O:30][C@H:31]2[C@H:44]([O:45][C:46](=[O:53])[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C@@H:43]([CH2:54][O:55][C:56](=[O:63])[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[O:42][C@H:33]([O:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C@H:32]2[O:64][C:65](=[O:72])[C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=2)[C@H:6]1[O:73][C:74](=[O:81])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1)C=C>CO.ClCCCl.[Pd](Cl)Cl>[C:74]([O:73][C@H:6]1[C@@H:5]([OH:4])[C@H:10]([O:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@@H:9]([CH2:20][O:21][C:22](=[O:29])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:8][C@@H:7]1[O:30][C@H:31]1[C@H:44]([O:45][C:46](=[O:53])[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C@@H:43]([CH2:54][O:55][C:56](=[O:63])[C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[O:42][C@H:33]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C@H:32]1[O:64][C:65](=[O:72])[C:66]1[CH:67]=[CH:68][CH:69]=[CH:70][CH:71]=1)(=[O:81])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of the allyl ether 49 (688 mg, 0.627 mmol) in MeOH (6 mL) and 1,2-dichloroethane (6 mL) (0.05 M) was treated with solid palladium chloride (25 mg). The mixture was stirred at 70° C. (external oil bath) for 2 h. TLC indicated complete conversion. The mixture was evaporated onto silica and purified by column chromatography (silica 2.7×17 cm, gradient elution with hexane-EtOAc 200:20, 200:40, 200:50, 210:70, 200:100) to give the alcohol 50 as a colourless gum (0.539 mg, 81%). 1H NMR (CDCl3, 400 MHz) δ 8.18-8.03 (m, 8H, Ph), 7.85-7.81 (m, 4H, Ph), 7.68-7.25 (m, 23H, Ph), 5.97 (dd or t, 1H, JH3(I)H4(I)=9.8, JH4(I)-H5(I)=9.8, H4I), 5.68 (dd, 1H, J JH1(I)-H2(I)=2.0, JH2(I)-H3(I)=2.9, H2I), 5.60 (dd or t, 1H, J JH3(II)-H4(II)=9.8, J JH4(II)-H5(II)=9.8, H4II), 5.28 (br s, 1H, H1II), 5.15 (d, 1H, J JH1(II)-H2(II)=2.0, H1I), 5.05 (dd, 1H, JH1(II)-H2(II)=2.0, JH2(II)-H3(II)=2.9, H2II), 4.77 (d, 1H, Jgem=11.7, CH2), 4.65-4.56 (m, 4H, CH2, H6Ieq, H3I and H6II), 4.44 (dd, 1H, Jgem=12.7, JH5(I)-H6(I)ax=4.9, H6Iax), 4.34 (m, 1H, H5II), 4.32 (dd, 1H, Jgem=10.7, JH5(II)-H6(II)=2.9, H6II), 4.28 (ddd, 1H, JH5(I)-H6(I)ax=4.9, JH5(I)-H6(I)eq=2.9, H5I), 4.17 (dd, 1H, H3II).

Workup

customThe mixture was evaporated onto silica
custompurified by column chromatography (silica 2.7×17 cm, gradient elution with hexane-EtOAc 200:20, 200:40, 200:50, 210:70, 200:100)

Sources & evidence

ORD record: ord-c337460b807449c1b9852381b3f341e4
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828952B2

Reaction notes

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