HCID 66863946, compound → HCID 87183063, compound

HRID 252673Notes

Reaction equation

HRID 252673 reaction equation
C(OCC(COC(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OC(=O)CCCCCCC/C=C\C/C=C\CCCCC)(=O)CCCCCCCCCCCCCCC.[C:62]([O:79][CH2:80][C@H:81]([CH2:102][O:103][C:104](=[O:106])[CH3:105])[O:82][C:83](=[O:101])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90]/[CH:91]=[CH:92]\[CH2:93]/[CH:94]=[CH:95]\[CH2:96][CH2:97][CH2:98][CH2:99][CH3:100])(=[O:78])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77]>>[C:62]([O:79][CH2:80][C@@H:81]([CH2:102][O:103][C:104](=[O:106])[CH3:105])[O:82][C:83](=[O:101])[CH2:84][CH2:85][CH2:86][CH2:87][CH2:88][CH2:89][CH2:90]/[CH:91]=[CH:92]\[CH2:93]/[CH:94]=[CH:95]\[CH2:96][CH2:97][CH2:98][CH2:99][CH3:100])(=[O:78])[CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH3:77]

Participants

3

Reactant 2

HCID 66863946HCID 66863946, compoundHCID 87183232HCID 87183232, compound

Product 1

HCID 87183063HCID 87183063, compoundYield 100%

Procedure

By using optically active (R)-1-palmitoyl glycerol and optically active (S)-1-palmitoyl glycerol as the starting materials, and by carrying out Example 1 and Example 3, respectively, heptane solutions of (R)-1-palmitoyl-2-linoleoyl-3-tritylglycerol and (S)-1-palmitoyl-2-linoleoyl-3-tritylglycerol were obtained. Except for using the optically active compounds instead of racemic 1-palmitoyl-2-linoleoyl-3-trityl-glycerol, (S)-1-palmitoyl-2-linoleoyl-3-acetyl-glycerol (45.8 g) and (R)-1-palmitoyl-2-linoleoyl-3-acetyl-glycerol (45.8 g) were obtained in the same manner as described in Preparation method-3 (theoretical amounts: 63.5 g, yield: 72.1%). (R)-enantiomer: {1H NMR (400 MHz, CDCl3): δ 0.85-0.92 (m, 6H), 1.20-1.33 (m, 38H), 1.62 (m, 4H), 2.03 (m, 4H), 2.07 (s, 3H), 2.36 (m, 4H), 2.77 (m, 2H), 4.14-4.31 (m, 4H), 5.23-5.36 (m, 5H)}, (S)-enantiomer: {1H NMR (400 MHz, CDCl3): δ 0.85-0.92 (m, 6H), 1.21-1.33 (m, 38H), 1.63 (m, 4H), 2.02 (m, 4H), 2.07 (s, 3H), 2.37 (m, 4H), 2.78 (m, 2H), 4.12-4.28 (m, 4H), 5.21-5.35 (m, 5H)}.

Sources & evidence

ORD record
ord-0e47b028b53841849ec4a06ff4b076dd
Source dataset
uspto-grants-2011_01
Patent number
US07868196B2

Reaction notes

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