Adipic acid monobenzyl ester → (S)-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxo-2-[5-oxo-5-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)pentanamido]pentanoic acid

HRID 1488267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1488267
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]([NH:10][CH2:11][CH2:12][O:13][C@H:14]1[O:33][C@H:32]([CH2:34][O:35][C@H:36]2[O:44][C@H:43]([CH2:45][OH:46])[C@@H:41]([OH:42])[C@H:39]([OH:40])[C@@H:37]2[OH:38])[C@@H:30]([OH:31])[C@H:17]([O:18][C@H:19]2[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]([OH:23])[C@@H:20]2[OH:21])[C@@H:15]1[OH:16])=[O:9])[C:3]([OH:5])=[O:4].[O:47]=[C:48]([NH:62][CH2:63][CH2:64][O:65][C@@H:66]1[O:74][C@@H:73]([CH3:75])[C@@H:71]([OH:72])[C@@H:69]([OH:70])[C@@H:67]1[OH:68])[CH2:49][CH2:50][CH2:51][C:52](ON1C(=O)CCC1=O)=[O:53].C(OC(=O)CCCCC(O)=O)C1C=CC=CC=1>CN(C=O)C>[C@H:19]1([O:18][C@H:17]2[C@H:30]([OH:31])[C@@H:32]([CH2:34][O:35][C@H:36]3[O:44][C@H:43]([CH2:45][OH:46])[C@@H:41]([OH:42])[C@H:39]([OH:40])[C@@H:37]3[OH:38])[O:33][C@H:14]([O:13][CH2:12][CH2:11][NH:10][C:8](=[O:9])[CH2:7][CH2:6][C@H:2]([NH:1][C:52](=[O:53])[CH2:51][CH2:50][CH2:49][C:48](=[O:47])[NH:62][CH2:63][CH2:64][O:65][C@@H:66]3[O:74][C@@H:73]([CH3:75])[C@@H:71]([OH:72])[C@@H:69]([OH:70])[C@@H:67]3[OH:68])[C:3]([OH:5])=[O:4])[C@H:15]2[OH:16])[O:27][C@H:26]([CH2:28][OH:29])[C@@H:24]([OH:25])[C@H:22]([OH:23])[C@@H:20]1[OH:21]

Komponenten

5

Edukt 3

HCID 11075409Adipic acid monobenzyl esterHCID 1179959412,5-dioxopyrrolidin-1-yl 5-oxo-5-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)pentanoateHCID 131736862(S)-2-amino-5-((2-((alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy)ethyl)amino)-5-oxopentanoic acid

Produkt 1

HCID 131736863(S)-5-[(2-{[alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl]oxy}ethyl)amino]-5-oxo-2-[5-oxo-5-({2-[(alpha-L-fucopyranosyl)oxy]ethyl}amino)pentanamido]pentanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of (S)-2-amino-5-[(2-{[α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranosyl]oxy}ethyl)amino]-5-oxopentanoic acid (350 mg, 4.75 mmol) in DMF (5 mL) at 0° C. was added 2,5-dioxopyrrolidin-1-yl 5-oxo-5-({2-[(α-L-fucopyranosyl)oxy]ethyl}amino)pentanoate (216 mg, 0.517 mmol, prepared according to Example 4, ML-4, Step A, substituting 5-(benzyloxy)-5-oxopentanoic acid for 6-(benzyloxy)-6-oxohexanoic acid and TEA (0.2 mL, 1.435 mmol). After stirring at 0° C. for 2 hr, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 silica gel (150 g), eluting with 5-40% AcCN in H2O to give the title compound. UPLC Method B: calculated for C38H65N3O26 979.39, observed m/e: 980.31 [M+1]; Rt=0.92 min.

Aufarbeitung

  1. customprepared
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by flash chromatography on C18 silica gel (150 g)
  4. washeluting with 5-40% AcCN in H2O

Quellen und Nachweise

ORD-Eintrag
ord-42f18ee05b014cfaa5cca83818f10288
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09427475B2

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