Hydrazine hydrate (1:1) → HCID 22806755, compound

HRID 1732792Notes

Reaction equation

HRID 1732792 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:23]([O:24][C@@H:25]2[O:33][C@H:32]([CH2:34][OH:35])[C@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]2[OH:27])[C@H:22]([O:36][C@@H:37]2[O:45][C@@H:44]([CH3:46])[C@@H:42]([OH:43])[C@@H:40]([OH:41])[C@@H:38]2[OH:39])[C@@H:21]([CH2:47][OH:48])[O:20][C@H:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=O)(=[O:3])[CH3:2].O.[NH2:50][NH2:51]>C(O)C>[C:1]([NH:4][C@@H:5]1[C@@H:23]([O:24][C@@H:25]2[O:33][C@H:32]([CH2:34][OH:35])[C@H:30]([OH:31])[C@H:28]([OH:29])[C@H:26]2[OH:27])[C@H:22]([O:36][C@@H:37]2[O:45][C@@H:44]([CH3:46])[C@@H:42]([OH:43])[C@@H:40]([OH:41])[C@@H:38]2[OH:39])[C@@H:21]([CH2:47][OH:48])[O:20][C@H:6]1[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:50][NH2:51])=[O:18])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22806758HCID 22806758, compound

Product 1

HCID 22806755HCID 22806755, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 8 (1 g) was dissolved in 85% hydrazine hydrate (4 ml) and allowed to stand for 4 h at ambient temperature. The reaction mixture was diluted with 95% ethanol (20 ml) and the solvents evaporated. The residue was dissolved in 10 ml water and dialyzed against 5 changes of water in an ultrafiltration cell. Lyophilization of the water gave 8-hydrazinocarbonyloctyl 2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-3-O-(β-D-galactopyranosyl)-β-D-glucopyranoside (14) in quantitative yield as an amorphous solid, [α]D --72.8° (c 1.0, water). This compound and the 5-hydrazinocarbonylpentyl analog were used to prepare the following Lewis-a antigens [Lea -O(CH2)8CONH]n -BSA where n can have any of the following values 11, 22, 30, or 45; [Lea -O(CH2)8CONH]28 -HSA; [Lea -O(CH2)8CONH]15 -polylysine; [Lea -O(CH2)8CONH(CH2)2NH]10 -dextran; [Lea -O(CH2)5CONH]n -BSA where n was 10 or 30; [Lea -O(CH2)5CONH]25 -HSA by the acyl azide method (cf example XII). The abbreviation Lea as used above stands for the Lewis-a trisaccharide determinant: ##STR12## Goat antiserum prepared against the natural Lewis-a blood group substance was found to form a precipitate with the above Lea antigens.

Workup

  1. customthe solvents evaporated
  2. dissolutionThe residue was dissolved in 10 ml water
  3. filtrationdialyzed against 5 changes of water in an ultrafiltration cell

Sources & evidence

ORD record
ord-d1527bbed0fb475d9401132f88b29ffb
Source dataset
uspto-grants-1980_12
Patent number
US04238473

Reaction notes

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