Diethylethanolamine → (2R)-3-[[(2R,3R,4S,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxyoxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acid

HRID 1603194Notes

Reaction equation

HRID 1603194 reaction equation
[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@@H:13]([NH:16][C:17]([CH3:19])=[O:18])[C@H:12]([O:20][C@H:21]3[C@@H:26]([O:27][P:28]([O:31][CH2:32][C@H:33]([O:37][CH2:38]/[CH:39]=[C:40](/[CH2:42][CH2:43]/[CH:44]=[CH:45]/[C:46]([CH2:49][CH2:50][C:51]([CH2:53]/[CH:54]=[C:55](/[CH2:57][CH2:58][CH:59]=[C:60]([CH3:62])[CH3:61])\[CH3:56])=[CH2:52])([CH3:48])[CH3:47])\[CH3:41])[C:34]([OH:36])=[O:35])([OH:30])=[O:29])[O:25][C@H:24]([C:63]([NH2:65])=[O:64])[C@:23]([OH:67])(C)[C@@H:22]3[O:68][C:69]([NH2:71])=[O:70])[O:11][C@@H:10]2[CH2:72][O:73][C@@H:74]2[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@H:76]([OH:83])[C@H:75]2[OH:84])[C@H:5]([NH:85][C:86]([CH3:88])=[O:87])[C@@H:4]([OH:89])[C@@H:3]1[O:90][C@@H:91]1[O:96][C@H:95]([C:97]([NH:99][C:100]2[C:104](=[O:105])[CH2:103][CH2:102][C:101]=2[OH:106])=[O:98])[C@H:94]([OH:107])[C@H:93]([OH:108])[C@H:92]1[OH:109].CCN(CCO)CC>>[CH3:1][C@H:2]1[O:7][C@@H:6]([O:8][C@H:9]2[C@H:14]([OH:15])[C@@H:13]([NH:16][C:17]([CH3:19])=[O:18])[C@H:12]([O:20][C@H:21]3[C@@H:26]([O:27][P:28]([O:31][CH2:32][C@@H:33]([O:37][CH2:38]/[CH:39]=[C:40](\[CH2:42][CH2:43]/[CH:44]=[CH:45]/[C:46]([CH2:49][CH2:50][C:51]([CH2:53]/[CH:54]=[C:55](/[CH2:57][CH2:58][CH:59]=[C:60]([CH3:61])[CH3:62])\[CH3:56])=[CH2:52])([CH3:47])[CH3:48])/[CH3:41])[C:34]([OH:36])=[O:35])([OH:30])=[O:29])[O:25][C@H:24]([C:63]([NH2:65])=[O:64])[C@@H:23]([OH:67])[C@@H:22]3[O:68][C:69]([NH2:71])=[O:70])[O:11][C@@H:10]2[CH2:72][O:73][C@@H:74]2[O:79][C@H:78]([CH2:80][OH:81])[C@@H:77]([OH:82])[C@H:76]([OH:83])[C@H:75]2[OH:84])[C@H:5]([NH:85][C:86]([CH3:88])=[O:87])[C@@H:4]([OH:89])[C@@H:3]1[O:90][C@@H:91]1[O:96][C@H:95]([C:97]([NH:99][C:100]2[C:101](=[O:106])[CH2:102][CH2:103][C:104]=2[OH:105])=[O:98])[C@H:94]([OH:107])[C@H:93]([OH:108])[C@H:92]1[OH:109]

Participants

3

Reactant 2

HCID 7497DiethylethanolamineHCID 73352825HCID 73352825, compound

Product 1

HCID 101098382(2R)-3-[[(2R,3R,4S,5S,6S)-3-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-carbamoyl-4-carbamoyloxy-5-hydroxyoxan-2-yl]oxy-hydroxyphosphoryl]oxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylidenenonadeca-2,6,13,17-tetraenoxy]propanoic acidYield 0.4%

Procedure

81 g of 95% pure moenomycin A dissolved in 7 L of aqueous buffer solution, pH 7.9, conductivity 10.5 mS/cm (resulting from DEAE purification and ultrafiltration), are loaded onto a column with a capacity of 2.7 L (W×H=10 cm×35 cm) and packed with MCI GEL® CHP20P. Elution is carried out with a linear gradient from buffer A (m/15 phosphate buffer, pH 7.8) to buffer B (m/15 phosphate buffer, pH 7.8 with 33% 2-propanol). The column flow is fractionated and analyzed. The fractions with at least 98.8% pure moenomycin A are collected and, after removal of the salts as described in Example 4, dried, resulting in 71 g of 99.3% pure moenomycin A with 0.4% moenomycin A12 as concomitant substance.

Workup

  1. washElution
  2. customThe fractions with at least 98.8% pure moenomycin A are collected
  3. customafter removal of the salts
  4. customdried

Sources & evidence

ORD record
ord-04c0781423f241079f278102e5b2623e
Source dataset
uspto-grants-1999_11
Patent number
US05986089

Reaction notes

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