2-Aminoethyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside → benzyl 6-({2-[(alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy]ethyl}amino)-6-oxohexanoate

HRID 1488238Notes

Reaction equation

HRID 1488238 reaction equation
[C@H:1]1([O:12][C@H:13]2[C@H:22]([OH:23])[C@@H:21]([CH2:24][O:25][C@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@@H:27]3[OH:28])[O:20][C@H:15]([O:16][CH2:17][CH2:18][NH2:19])[C@H:14]2[OH:37])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3].O=C1CCC(=O)N1[O:45][C:46](=O)[CH2:47][CH2:48][CH2:49][CH2:50][C:51]([O:53][CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)=[O:52]>CN(C=O)C>[C@H:1]1([O:12][C@H:13]2[C@H:22]([OH:23])[C@@H:21]([CH2:24][O:25][C@H:26]3[O:34][C@H:33]([CH2:35][OH:36])[C@@H:31]([OH:32])[C@H:29]([OH:30])[C@@H:27]3[OH:28])[O:20][C@H:15]([O:16][CH2:17][CH2:18][NH:19][C:46](=[O:45])[CH2:47][CH2:48][CH2:49][CH2:50][C:51]([O:53][CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[O:52])[C@H:14]2[OH:37])[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:2]1[OH:3]

Participants

4

Reactant 2

HCID 117136792-Aminoethyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranosideHCID 117996037Benzyl (2,5-dioxopyrrolidin-1-yl) adipate

Product 1

HCID 117995912benzyl 6-({2-[(alpha-D-mannopyranosyl-(1->3)-[alpha-D-mannopyranosyl-(1->6)]-alpha-D-mannopyranosyl)oxy]ethyl}amino)-6-oxohexanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-aminoethyl α-D-mannopyranosyl-(1→3)-[α-D-mannopyranosyl-(1→6)]-α-D-mannopyranoside (1.23 g, 2.247 mmol, WO 2010/088294 A1) in DMF (20 mL) at 0° C. was added benzyl 6-[(2,5-dioxopyrrolidin-1-yl)oxy]-6-oxohexanoate (1.02 g, 3.06 mmol) and TEA (0.5 mL, 3.59 mmol). After stirring at 0° C. for 1 hour, the reaction mixture was concentrated and the residue was purified by flash chromatography on C18 reverse silica gel column (275 g), eluting with 0-40% AcCN in H2O to give the title compound. UPLC Method B: calculated for C33H51NO19 765.31, observed m/e=766.26 [M+1]; Rt=4.04 min. 1H NMR (D2O) δ 7.43-7.37 (5H, m), 5.14 (2H, s), 5.07-5.06 (1H, m), 4.82-4.81 (1H, m), 4.77-4.76 (1H, m), 4.06-4.01 (2H, m), 3.96-3.92 (2H, m), 3.87-3.81 (5H, m), 3.79-3.77 (1H, m), 3.74-3.67 (5H, m), 3.65-3.60 (4H, m), 3.53-3.49 (1H, m), 3.37-3.35 (2H, m), 2.43-2.40 (2H, m), 2.22-2.19 (2H, m), 1.62-1.52 (4H, m).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash chromatography on C18 reverse silica gel column (275 g)
  3. washeluting with 0-40% AcCN in H2O

Sources & evidence

ORD record
ord-c1631a28ecdf40239b07c4dd99ed09b3
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

Loading…