Methyl L-threoninate hydrochloride → N-(cis4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-L-Threonine

HRID 650787Notes

Reaction equation

HRID 650787 reaction equation
[C:1]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[CH2:24][O:25][P:26]([OH:29])([OH:28])=[O:27])(=[O:21])[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][CH:8]=[CH:9][CH2:10][CH:11]=[CH:12][CH2:13][CH:14]=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].[C:33](O)(=O)[CH2:34]C/C=C\CC=CCC=CCC=CCC=CCC=CCC.Cl.[CH3:58]OC(=O)[C@H]([C@@H](C)O)N>>[C:1]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[C@@H:24]([CH3:58])[O:25][P:26]([OH:29])([OH:28])=[O:27])(=[O:21])[CH2:2][CH2:3]/[CH:4]=[CH:5]\[CH2:6][CH:7]=[CH:8][CH2:9][CH:10]=[CH:11][CH2:12][CH:13]=[CH:14][CH2:15][CH:16]=[CH:17][CH2:18][CH:19]=[CH:20][CH2:33][CH3:34]

Participants

4

Reactant 3

HCID 2734893Methyl L-threoninate hydrochlorideHCID 730132534,7,10,13,16,19-cis-Docosahexaenoic acidHCID 86583929N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Serine

Product 1

HCID 86583932N-(cis4,7,10,13,16,19-Docosahexaenoyl)-O-Phospho-L-Threonine

Procedure

This compound was prepared as described above for (6) using 0.5 nmmol (164 mg) of cis-4,7,10,13,16,19-docosahexaenoic acid and 1 mmol (170 mg) of L-threonine methyl ester hydrochloride; yield 109 mg, (43%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 1.2-1.4 (3H, d, CH3CHOP); 2.0-2.1 (t, 2H, CH2CO); 2.2-2.4 (m, 4H, 2CH2CH═CH); 2.7-2.9 (br s, 10H, 5HC═CHCH2CH═CH); 4.1-4.3 (m, 2H, 2CH); 5.2-5.4 (br s, 12H, 6HC═CH); 8.2-8.4 (m, 3H, NH and 2POH)

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-1b704c20f5a24b9cb585cda654d75e94
Source dataset
uspto-grants-2001_08
Patent number
US06274747B1

Reaction notes

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