1,2-Di-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol → 1,2-Di-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerol

HRID 2407350Notes

Reaction equation

HRID 2407350 reaction equation
[C:1]([O:20][CH2:21][CH:22]([O:36][C:37](=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47]/[CH:48]=[CH:49]\[CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH3:54])[CH2:23][O:24][C@@H:25]1[O:33][C@H:32]([CH2:34][OH:35])[C@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]1[OH:27])(=[O:19])[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].[C:56]([O:75][CH2:76][CH:77]([O:91][C:92](=[O:110])[CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99]/[CH:100]=[CH:101]\[CH2:102]/[CH:103]=[CH:104]\[CH2:105]/[CH:106]=[CH:107]\[CH2:108][CH3:109])[CH2:78][O:79][C@@H:80]1[O:88][C@H:87]([CH2:89][OH:90])[C@@H:85]([OH:86])[C@H:83]([OH:84])[C@H:81]1[OH:82])(=[O:74])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]\[CH2:66]/[CH:67]=[CH:68]\[CH2:69]/[CH:70]=[CH:71]\[CH2:72][CH3:73].C(O[CH2:131][CH:132]([O:146][C:147](=[O:165])[CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154]/[CH:155]=[CH:156]\[CH2:157]/[CH:158]=[CH:159]\[CH2:160]/[CH:161]=[CH:162]\[CH2:163][CH3:164])[CH2:133]O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC.[C:166](OCC(OC(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC)CO[C@@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O)(=O)[CH2:167][CH2:168][CH2:169][CH2:170][CH2:171][CH2:172][CH2:173]/[CH:174]=[CH:175]\[CH2:176]/[CH:177]=[CH:178]\[CH2:179]/[CH:180]=C\CC.C(OCC(OC(=O)CCCCCCC/C=C\C/C=C\C/C=C\CC)CO[C@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O)(=[O:250])CCCCCCC/C=C\C/C=C\C/C=C\CC>>[C:1]([O:20][CH2:21][CH:22]([O:36][C:37](=[O:55])[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]/[CH:45]=[CH:46]\[CH2:47]/[CH:48]=[CH:49]\[CH2:50]/[CH:51]=[CH:52]\[CH2:53][CH3:54])[CH2:23][O:24][C@@H:25]1[O:33][C@H:32]([CH2:34][OH:35])[C@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]1[OH:27])(=[O:19])[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].[C:56]([O:75][CH2:76][CH:77]([O:91][C:92](=[O:110])[CH2:93][CH2:94][CH2:95][CH2:96][CH2:97][CH2:98][CH2:99]/[CH:100]=[CH:101]\[CH2:102]/[CH:103]=[CH:104]\[CH2:105]/[CH:106]=[CH:107]\[CH2:108][CH3:109])[CH2:78][O:79][C@@H:80]1[O:88][C@H:87]([CH2:89][OH:90])[C@@H:85]([OH:86])[C@H:83]([OH:84])[C@H:81]1[OH:82])(=[O:74])[CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63]/[CH:64]=[CH:65]\[CH2:66]/[CH:67]=[CH:68]\[CH2:69]/[CH:70]=[CH:71]\[CH2:72][CH3:73].[C@@H:25]1([O:24][CH:23]([CH2:180][CH2:179][CH2:178][CH2:177][CH2:176]/[CH:175]=[CH:174]\[CH2:173]/[CH:172]=[CH:171]\[CH2:170]/[CH:169]=[CH:168]\[CH2:167][CH3:166])[CH:22]([CH2:131][CH:132]([O:146][C:147](=[O:165])[CH2:148][CH2:149][CH2:150][CH2:151][CH2:152][CH2:153][CH2:154]/[CH:155]=[CH:156]\[CH2:157]/[CH:158]=[CH:159]\[CH2:160]/[CH:161]=[CH:162]\[CH2:163][CH3:164])[CH3:133])[C:21]([O-:20])=[O:250])[O:33][C@H:32]([CH2:34][OH:35])[C@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]1[OH:27]

Participants

8

Reactant 5

HCID 52822871,2-Di-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerolHCID 10102343HCID 10102343, compoundHCID 44431806HCID 44431806, compoundHCID 131731784HCID 131731784, compoundHCID 131731785HCID 131731785, compound

Product 3

HCID 52822871,2-Di-(9Z,12Z,15Z-octadecatrienoyl)-3-O-beta-D-galactosyl-sn-glycerolHCID 44431806HCID 44431806, compoundHCID 131731782HCID 131731782, compound

Procedure

Even more specific examples of the glycoside of a mono- or diacylglycerol compound are 3 β-D-galactopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate, 3-β-D-glucopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate, 3-α-D-galactopyranosyloxy-2-(octadeca-9Z,I2Z,I5Z trienoyloxy) propanyl octadeca-9Z,12Z,15Z-trienoate, 3-α-D-glucopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate, 6-O-(α-D-galactopyranosyl)-3 β-D-galactopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,I5Z-trienoate and 6-O-(α-D-galactopyranosyl)-3-α-D-galactopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate, such as 3-β-D-galactopyranosyloxy-2-(octadeca-9Z,I2Z,I5Z-trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate or 3-β-D-glucopyranosyloxy-2-(octadeca-9Z,12Z,15Z trienoyloxy)propanyl octadeca-9Z,12Z,15Z-trienoate, e.g. 3-β-D-galactopyranosyloxy-2-(octadeca-9Z,12Z,15Z-trienoyloxy)propanyloctadeca-9Z,I 2Z,15Z-trienoate which can be isolated from rose-hips.

Sources & evidence

ORD record
ord-71edd9f2a20d46dc8729757fb8806d6e
Source dataset
uspto-grants-2014_08
Patent number
US08809522B2

Reaction notes

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