N2,N5-Bis[3-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosylthio)propionyl]-L-ornithine → N2,N5-Bis[3-(alpha-D-mannopyranosylthio)propionyl)-L-ornithine

HRID 851681Notes

Reaction equation

HRID 851681 reaction equation
C([O:4][C@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@@H:6]1[S:24][CH2:25][CH2:26][C:27]([NH:29][C@H:30]([C:63]([OH:65])=[O:64])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:62])[CH2:36][CH2:37][S:38][C@H:39]1[O:56][C@H:55]([CH2:57][O:58]C(=O)C)[C@@H:50]([O:51]C(=O)C)[C@H:45]([O:46]C(=O)C)[C@@H:40]1[O:41]C(=O)C)=[O:28])(=O)C>CO.O.CCN(CC)CC>[C@H:6]1([S:24][CH2:25][CH2:26][C:27]([NH:29][C@H:30]([C:63]([OH:65])=[O:64])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[O:62])[CH2:36][CH2:37][S:38][C@H:39]2[O:56][C@H:55]([CH2:57][OH:58])[C@@H:50]([OH:51])[C@H:45]([OH:46])[C@@H:40]2[OH:41])=[O:28])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@@H:5]1[OH:4]

Participants

3

Reactant 1

HCID 86738906N2,N5-Bis[3-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosylthio)propionyl]-L-ornithine

Product 1

HCID 57035602N2,N5-Bis[3-(alpha-D-mannopyranosylthio)propionyl)-L-ornithineYield 100%

Reagents, catalysts & solvents 1

HCID 23434731Methanol water triethylamineSolvent

Procedure

A solution of 36 (100 mg) in MeOH-H2O-Et3N 5:4:1 (v/v/v, 3 ml) is kept for 3 hours at room temperature, and evaporated to a residue which is put on a Sephadex G-25 column and eluted with water. The desired fractions are combined and lyophilized to give the title compound (65 mg, 100%): NMR (D2O)δ: 5.38 (d, J1,2 =15 Hz), 5.35 (d,J1,2 =1.5 Hz) (H-1), 2.70 (t), 2.63 (t) (SCH2CH2).

Workup

  1. customevaporated to a residue which
  2. washeluted with water

Sources & evidence

ORD record
ord-e0c767f3b17d40e6a0f9c764c06432f7
Source dataset
uspto-grants-1983_05
Patent number
US04386026

Reaction notes

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