alpha-D-Galactopyranose → p-Nitrophenyl 3-O-alpha-D-galactopyranosyl-alpha-D-galactopyranoside

HRID 2184650

Reaction equation

HRID 2184650 reaction equation
O[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O.[C@@H]1(O[C@H]2[C@@H](O)[C@@H](CO)O[C@H](OC3C=CC(N)=CC=3)[C@@H]2O)O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O.[C@@H:43]1([O:54][C@H:55]2[C@@H:70]([OH:71])[C@@H:69]([CH2:72][OH:73])[O:68][C@H:57]([O:58][C:59]3[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=3)[C@@H:56]2[OH:74])[O:51][C@H:50]([CH2:52][OH:53])[C@H:48]([OH:49])[C@H:46]([OH:47])[C@H:44]1[OH:45]>CO.[Pd]>[C@H:43]1([O:54][C@H:55]2[C@@H:70]([OH:71])[C@@H:69]([CH2:72][OH:73])[O:68][C@H:57]([O:58][C:59]3[CH:64]=[CH:63][C:62]([N+:65]([O-:67])=[O:66])=[CH:61][CH:60]=3)[C@@H:56]2[OH:74])[O:51][C@H:50]([CH2:52][OH:53])[C@H:48]([OH:49])[C@H:46]([OH:47])[C@H:44]1[OH:45]

Participants

6

Reactant 3

HCID 439357alpha-D-GalactopyranoseHCID 69753196p-nitrophenyl 3-O-beta-galactopyranosyl-alpha-D-galactopyranosideHCID 69753278p-aminophenyl 3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

Product 1

HCID 11454026p-Nitrophenyl 3-O-alpha-D-galactopyranosyl-alpha-D-galactopyranoside

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A reaction scheme illustrating the chemoenzymatic synthesis of the αGal epitope, p-aminophenyl 3-O-β-D-galactopyranosyl-α-D-galactopyranoside (22) is shown in FIG. 3. p-Nitrophenyl 3-O-α-D-galactopyranosyl-α-D-galactopyranoside (compound 21) was prepared enzymatically as described by Nilsson (Tetrahedron Lett. (1997) 38:133-136). A mixture of p-nitrophenyl 3-O-β-galactopyranosyl-α-D-galactopyranoside (70 mg, 0.15 mmol) and 10 mg Pd/C (10%) in methanol (4 mL) was stirred under hydrogen at room temperature overnight. The reaction mixture was then filtered through Celite and the filtrate was concentrated in vacuo to give (50 mg) as a yellowish solid: 1H NMR (CD3OD): δ 6.87 (t, 2 H), 6.57 (d, 2 H), 5.21 (d, 1 H), 4.98 (d, 1 H), 4.2-4.1 (m, 2 H), 4.1-3.8 (m, 3 H), 3.8-3.7 (m, 3 H), 3.7-3.5 (m,4 H); 13C NMR (CD3OD): δ 143.8, 120.1, 117.9, 115.4, 101.2, 97.6, 78.3, 77.0, 72.6, 71.5, 71.4, 70.3, 68.7, 67.4, 63.2, 62.6; MS (ESI): m/e (M+Na+) Calcd. for C18H27NO11Na: 456.2, obsd: 456.2.

Workup

  1. customA reaction scheme
  2. filtrationThe reaction mixture was then filtered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give (50 mg) as a yellowish solid

Sources & evidence

ORD record
ord-f7da1507dadb4a6699bb21d707922e8d
Source dataset
uspto-grants-2002_06
Patent number
US06399578B1

Linked notes

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