HCID 10841777, compound → HCID 10676823, compound
Reaction equation
[CH2:1]([O:17][CH2:18][C@H:19]([CH2:22][OH:23])[O:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].ClC(Cl)(Cl)C(=N)O[CH:28]1[O:53][C@H:52]([CH2:54][O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C@@H:43]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C@H:34]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C@H:29]1[O:30][C:31](=[O:33])[CH3:32]>>[CH2:1]([O:17][CH2:18][C@H:19]([CH2:22][O:23][C@@H:28]1[O:53][C@H:52]([CH2:54][O:55][CH2:56][C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)[C@@H:43]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C@H:34]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[C@H:29]1[O:30][C:31](=[O:33])[CH3:32])[O:20][CH3:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
3
Procedure
1-O-Hexadecyl-2-O-methyl-sn-glycerol (433.3 mg, 1.3 mmol) prepared as described above, was glucosylated with 2-O-acetyl-3,4,6-tri-O-benzyl-α, β-D-glucopyranosyl trichloroacetimidate (930 mg, 1.4 mmol) to give 1-O-Hexadecyl-2-O-methyl-3-O-(2′-O-acetyl-3′,4′,6′-tri-O-benzyl-β-D-glucopyranosyl)-sn-glycerol in 76% yield (805 mg). [α]D −8.5 deg. 1H-NMR: δ7.32-7.15 (m, 15H, 3PhCH2) 4.99 (dd, 1H, J1′,2a′=2.5 Hz, J1′,2e′−1.0 Hz, H-1′), 3.93 (m, 1H, H-5′), 3.44 (s, 3H, OCH3), 2.15 (ddd, 1H, J2e′,3′=4.7 Hz, J2e′,2a′=11.5 Hz,H-2e′), 1.7 (ddd, 1H, H-2a′, 1.25 (s, 26H, CH2), 0.87 (t, 3H, CH3). 13C-NMR: δ98.05 (C-1′), 79.33, (C-5′), 62.07 (C-6′), 57.94 (OCH3), 37.36 (C-2′), 31.90, 29.64, 29.48, 29.31, 26.06, 22.67 (CH2), 14.06 (CH3).
Sources & evidence
- ORD record
- ord-11a7fbda679145bda809fa03acce9cd2
- Source dataset
- uspto-grants-2003_06
- Patent number
- US06573246B1
Reaction notes
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