Methanesulfonyl chloride → (+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerol

HRID 977285Notes

Reaction equation

HRID 977285 reaction equation
[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][O:23][S:24]([CH3:27])(=[O:26])=[O:25])[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].[CH2:28](SCC(CO)OCC)CCCCCCCCCCCCCCC.CS(Cl)(=O)=O>>[CH2:1]([S:17][CH2:18][CH:19]([CH2:22][O:23][S:24]([CH3:27])(=[O:26])=[O:25])[O:20][CH2:21][CH3:28])[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

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 14282492(+/-)-1-S-hexadecyl-2-O-ethylthioglycerolHCID 14522778(+/-)-1-S-hexadecyl-2-O-methyl-3-O-mesylthioglycerol

Product 1

HCID 14522779(+/-)-1-S-hexadecyl-2-O-ethyl-3-O-mesylthioglycerolYield 94%

Procedure

This compound was prepared in an analogous manner to that of (±)-1-S-hexadecyl-2-O-methyl-3-O-mesylthioglycerol from 5.5 grams (0.016 mole) of (±)-1-S-hexadecyl-2-O-ethylthioglycerol and 2.2 grams (0.019 mole) of methanesulfonyl chloride. This resulted in 6.2 grams of product (94%) as an oil. 1H-NMR (CDCl3): delta, 0.87(t, 3H, terminal methyl), 1.2-1.6[m, 31H, (CH2)14, CH3 --CH2 --O], 2.58(m, 2H, S--CH2), 2.62(m, 2H, CH--CH2 --S), 3.08(s, 3H, SO2 --CH3), 3.40-3.50(m, 3H, CH, CH3 --CH2 --O), 4.35(m, 2H, CH2 --OSO2).

Sources & evidence

ORD record
ord-956aa47129c74903ab37d809345905b5
Source dataset
uspto-grants-1997_03
Patent number
US05614548

Reaction notes

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