Pyridine → HCID 86621844, compound

HRID 1713581Notes

Reaction equation

HRID 1713581 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]1([CH2:42][CH2:43][OH:44])[O:40][CH3:41])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[S:51](Cl)([C:54]1[CH:60]=[CH:59][C:57]([CH3:58])=[CH:56][CH:55]=1)(=[O:53])=[O:52]>C(Cl)Cl>[CH3:58][C:57]1[CH:59]=[CH:60][C:54]([S:51]([O:44][CH2:43][CH2:42][C@@:10]2([O:40][CH3:41])[C@H:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C@@H:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C@H:13]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[O:11]2)(=[O:53])=[O:52])=[CH:55][CH:56]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chloride2×HCID 68792359HCID 68792359, compound

Product 1

HCID 86621844HCID 86621844, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2-((2S,3R,4S,5R,6R)-3,4,5-Tris(benzyloxy)-6-(benzyloxymethyl)-2-methoxytetrahydro-2H-pyran-2-yl)ethanol (8) (0.46 g, 0.77 mmol) was dissolved in CH2Cl2 (2 mL). Pyridine (0.31 mL, 3.85 mmol) and TsCl (0.29 g, 1.54 mmol) were added and the reaction mixture was heated at 50° C. for 18 h. Additional TsCl (0.05 g, 0.26 mmol) was then added and the reaction mixture was heated at 50° C. for another 4 hours. The mixture was concentrated onto celite and chromatographed over SiO2, (ISCO system, 0-40% EtOAc/hexanes) to provide an oil (0.317 g, 55%). 1H NMR (300 MHz, CDCl3) δ ppm: 7.66 (d, J=8.4 Hz, 2H), 7.14-7.32 (m, 22H), 4.77-4.89 (m, 4H), 4.46-4.57 (m, 4H), 3.86-4.07 (m, 1H), 3.48-3.64 (m, 4H), 3.31 (d, J=9.3 Hz, 1H), 3.17 (s, 3H), 2.36 (s, 3H), 2.13 (t, J=8.1 Hz, 1H). LC/MS tR=3.37 min, calcd for C44H48O9S: 752.3, found 775.2 (M+Na)+.

Workup

  1. temperaturethe reaction mixture was heated at 50° C. for another 4 hours
  2. concentrationThe mixture was concentrated onto celite
  3. customchromatographed over SiO2, (ISCO system, 0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-53197708a1614ee5bc08a2538dad95c3
Source dataset
uspto-grants-2010_09
Patent number
US07795228B2

Reaction notes

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