9,12,15-cis-Octadecatrienoic acid → N-(cis-9,12,15-Octadecatrienoyl)-O-phospho-L-Threonine

HRID 650794Notes

Reaction equation

HRID 650794 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]CC.[C:33](O)(=O)CCCCCCC/C=C\CC=CCC=CCC.Cl.COC(=O)[C@H]([C@@H](C)O)N>>[C:1]([NH:22][C@H:23]([C:30]([OH:32])=[O:31])[C@@H:24]([CH3:33])[O:25][P:26]([OH:29])([OH:28])=[O:27])(=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH:12]=[CH:13][CH2:14][CH:15]=[CH:16][CH2:17][CH3:18]

Participants

4

Reactant 3

HCID 4456409,12,15-cis-Octadecatrienoic acidHCID 2734893Methyl L-threoninate hydrochlorideHCID 86583929N-(cis-5,8,11,14-Eicosatetraenoyl)-O-Phospho-L-Serine

Product 1

HCID 86583937N-(cis-9,12,15-Octadecatrienoyl)-O-phospho-L-Threonine

Procedure

This compound was prepared as described above for (6), using 0.5 mmol (139 mg) of cis-9,12,15-octadecatrienoic acid and 1 mmol (170 mg) of L-threonine methyl ester hydrochloride; yield 85 mg (37%); Rf 0.05-0.10 (system B); 1H-NMR (CD3SOCD3, 200 MHz) δ0.9-1.0 (t, 3H, ω-CH3); 1.3-1.5 (m, 13H, 5CH2 and CH3CHOP); 2.0-2.2 (m, 6H, CH2CO and 2CH2CH═CH); 2.7-2.9 (br s, 4H, 2HC═CH—CH2—CH═CH); 4.1-4.3 (m, 2H, 2CH); 5.2-5.4 (br s, 6H, 3HC═CH); 8.2-8.4 (m, 3H, NH and 2POH)

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-77364808adbc41cf82af204f72d8d8be
Source dataset
uspto-grants-2001_08
Patent number
US06274747B1

Reaction notes

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