Ethyl 2-acetamido-2-deoxy-3,6-di-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]-beta-glucopyranoside → alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-GlcNAc-OEt

HRID 653340Notes

Reaction equation

HRID 653340 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:13]([O:14]C(=O)C)[C@H:12]([O:18][C@@H:19]2[O:56][C@H:55]([CH2:57][O:58]C(=O)C)[C@H:30]([O:31][C@H:32]3[O:49][C@H:48]([CH2:50][O:51]C(=O)C)[C@H:43]([O:44]C(=O)C)[C@H:38]([O:39]C(=O)C)[C@H:33]3[O:34]C(=O)C)[C@H:25]([O:26]C(=O)C)[C@H:20]2[O:21]C(=O)C)[C@@H:11]([CH2:62][O:63]C(=O)C)[O:10][C@H:6]1[O:7][CH2:8][CH3:9])(=[O:3])[CH3:2]>C[O-].[Na+]>[C:1]([NH:4][C@@H:5]1[C@@H:13]([OH:14])[C@H:12]([O:18][C@@H:19]2[O:56][C@H:55]([CH2:57][OH:58])[C@H:30]([O:31][C@H:32]3[O:49][C@H:48]([CH2:50][OH:51])[C@H:43]([OH:44])[C@H:38]([OH:39])[C@H:33]3[OH:34])[C@H:25]([OH:26])[C@H:20]2[OH:21])[C@@H:11]([CH2:62][OH:63])[O:10][C@H:6]1[O:7][CH2:8][CH3:9])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 88636952Ethyl 2-acetamido-2-deoxy-3,6-di-O-acetyl-4-O-[2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]-beta-glucopyranoside

Product 1

HCID 18608320alpha-D-Gal-(1->4)-beta-D-Gal-(1->4)-beta-D-GlcNAc-OEtYield 61%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Compound 87 (58 mg, 0.06 mmol) was O-deacetylated in methanolic sodium methoxide (0.036M, 5.5 ml) at room temperature for 21 h. The mixture was neutralized with Duolite C-26 (H) resin, filtered and concentrated. The residue was dissolved in water and lyophilized to give 88 (21 mg, 60%) with [α]D22 +25° (c 0.7, water). 1H-NMR [(CD3)2SO+D2O, 50°, Me4Si] δ inter alia 4.80 (d, 1H, J=3.5 Hz, H1"), 4.37 (d, 1H, J=8 Hz, H1 or H1'), 4.29 (d, 1H, J=7.5 Hz, H1 or H1'), 4.07 (bt, 1H, J~6.5 Hz), 1.81 (s, 3H, MeCON), 1.08 (t, 3H, J=7 Hz, CH3CH 2). 13C-NMR (D2O, TSP) δ 177.4, 106.1, 103.4, 103.1, 81.6, 80.1, 78.2, 77.7, 75.4, 75.0, 73.7, 73.6, 72.0, 71.7, 71.4, 69.1 (CH2), 63.3 (CH2), 63.2 (CH2), 62.9 (CH2), 58.1, 25.0, 17.1. b: Compound 86 (15 mg, 0.017 mmol) was O-deacetylated and worked-up as above to give 88 (8.0 mg, 81%).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-202ce003b7b0400b820ca53a50300855
Source dataset
uspto-grants-1987_06
Patent number
US04675392

Reaction notes

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