Methanesulfonate → HCID 54191993, compound

HRID 1781260Notes

Reaction equation

[C:1]([O:4][C@H:5]1[C@H:23]([OH:24])[C@@H:22]([CH2:25][OH:26])[O:21][C@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C@@H:6]1[O:27][C@H:28]1[O:57][C@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@H:38]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:29]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:3])[CH3:2].[S:63]([O-])(=[O:66])(=[O:65])[CH3:64]>>[C:1]([O:4][C@H:5]1[C@H:23]([OH:24])[C@@H:22]([CH2:25][O:26][S:63]([CH3:64])(=[O:66])=[O:65])[O:21][C@H:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C@@H:6]1[O:27][C@H:28]1[O:57][C@H:56]([CH2:58][O:59][C:60](=[O:62])[CH3:61])[C@@H:47]([O:48][CH2:49][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[C@H:38]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@H:29]1[O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 85257Methanesulfonate

HCID 70131555HCID 70131555, compound

Product 1

HCID 54191993HCID 54191993, compoundYield 85.3%

Procedure

Compound 24 (570 mg, 0.66 mmol) was converted into its methane sulfonyl derivative exactly as described for the preparation of 10 to give 25 (530 mg, 85.3%) as a syrup after chromatography on silica gel using (hexane:ethyl acetate; 3:2) as eluant; [α]D +76.6° (c 0.57, chloroform). 1H-n.m.r. (CDCl3): δ5.19(t, 1H, J2,3 =J3,4 10.0 Hz, H-3), 4.90(d, 1H, J1',2' 3.8 Hz, H-1'), 4.82(d, 1H, J1,2 3.8 Hz, H-1), 3.57(s, 3H, OCH3), 3.00(s, 3H, CH3SO2), 2.23 and 2.03(s, 3H each, 2×Ac).

Sources & evidence

ORD record: ord-7adcf7d8bf834507a9a5cff0f9c64b36
Source dataset: uspto-grants-1997_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05633233

Reaction notes

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