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

HRID 2184650

반응식

HRID 2184650 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f7da1507dadb4a6699bb21d707922e8d
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399578B1

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