Pyridine → HCID 86597507, compound

HRID 2055063Notes

Reaction equation

HRID 2055063 reaction equation
[C:1]([C:4]([C@@H:6]([C@:8]([C:22](=[O:24])[CH3:23])([C@@:10]([C:19](=[O:21])[CH3:20])([C@@H:12]([CH:14]([C:16](=[O:18])[CH3:17])[OH:15])[OH:13])[OH:11])[OH:9])[OH:7])=[O:5])(=[O:3])[CH3:2].N1C=CC=CC=1.[N:31]([CH2:34][CH2:35][CH2:36][C:37](Cl)=[O:38])=[N+:32]=[N-:33].C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:31]([CH2:34][CH2:35][CH2:36][C:37]([C@:12]([C@:10]([C:19](=[O:21])[CH3:20])([C@@:8]([C:22](=[O:24])[CH3:23])([C@@H:6]([CH:4]([C:1](=[O:3])[CH3:2])[OH:5])[OH:7])[OH:9])[OH:11])([OH:13])[C:14]([C:16](=[O:18])[CH3:17])=[O:15])=[O:38])=[N+:32]=[N-:33]

Participants

6

Reactant 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 11105514HCID 11105514, compoundHCID 86597508HCID 86597508, compound

Product 1

HCID 86597507HCID 86597507, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3,4,6 tetraacetyl D-glucose (W. E. Dick, Carbohyd. Res., 21, 255-268 (1972)) is dissolved in CH2Cl2 to make a 0.1M solution. 6 eqivalents of pyridine and 3 equivalents of 4-azidobutyryl chloride (S. Kusumoto et. al., Bull. Chem. Soc. Jpn., 59, 1289-1298 (1986)) are added. After several hours, the reaction is poured into saturated NaHCO3, extracted with CH2Cl2, dried over Na2SO4, and concentrated. The residue is purified by flash chromatography to give the title compound.

Workup

  1. waitAfter several hours
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-b484409001de4d20923c943ab62b3a36
Source dataset
uspto-grants-2008_02
Patent number
US07331920B2

Reaction notes

Loading…