Cesium carbonate → HCID 54096342, compound

HRID 1608093Notes

Reaction equation

HRID 1608093 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@@H:30]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[O:29][C@H:6]1[O:7][CH2:8][CH2:9][S:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=O)=O)(=[O:3])[CH3:2].C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1OCCBr)(=O)C.C(S)CCCCCCCCCCCCCCC.C(=O)([O-])[O-].[Cs+].[Cs+]>CCCCCC.C(OC(=O)C)C.O.ClCCl.CN(C)C=O>[C:1]([O:4][C@@H:5]1[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:31]([O:37][C:38](=[O:40])[CH3:39])[C@@H:30]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[O:29][C@H:6]1[O:7][CH2:8][CH2:9][S:10][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:3])[CH3:2]

Participants

10

Reactant 4

HCID 10796Cesium carbonateHCID 18015HexadecanethiolHCID 10623633HCID 10623633, compoundHCID 56633597HCID 56633597, compound

Product 1

HCID 54096342HCID 54096342, compoundYield 64%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Hexadecylsulfonyl)ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside. 2-Bromoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (Dahmen et al. Carbohydr. Res., 116 (1983)) (540 mg, 1.19 mmol), hexadecanethiol (383 mg, 1.49 mmol), cesium carbonate (292 mg, 0.89 mmol) and dimethylformamide (5 ml) was stirred overnight. Dichloromethane (75 ml) and water (40 ml) were added. The aqueous phase was extracted with dichloromethane (2×25 ml), the combined organic phases were dried (Na2SO4) and concentrated. Chromatography (SiO2 ; ethylacetate: hexane) gave pure 2-(hexadecylthio)ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (480 mg, 0.76 mmol, 64%), which was dissolved in ethyl acetate (12 ml) and treated with m-chloroperbenzoic acid (1.71 mmol). After 4 hours the solvents were removed and the residue was dissolved in dichloromethane and filtered through alumina (10 g) to give the pure sulfone lipid (495 mg, 98%). [α]D23 =-8.7° (c=0.9 in CDCl3).

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane (2×25 ml)
  2. dry with materialthe combined organic phases were dried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2cf32bcc55284b078af4869ffd7a4bc8
Source dataset
uspto-grants-1989_09
Patent number
US04868289

Reaction notes

Loading…