(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 135890153, compound

HRID 539875Notes

Reaction equation

HRID 539875 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][CH3:22])=[C:6]([C:8]2[NH:13][C:12](=[O:14])[C:11]([Br:15])=[C:10]([CH:16]([CH3:18])[CH3:17])[N:9]=2)[CH:7]=1.[O:23]=[CH:24][C@@H:25]([C@H:27]([C@@H:29]([C@@H:31]([CH2:33][OH:34])[OH:32])[OH:30])[OH:28])O>C(O)CCC.C(O)(=O)C>[Br:15][C:11]1[C:12](=[O:14])[NH:13][C:8]([C:6]2[CH:7]=[C:2]([NH:1][CH:33]3[CH:31]([OH:32])[CH:29]([OH:30])[CH:27]([OH:28])[CH:25]([CH2:24][OH:23])[O:34]3)[CH:3]=[CH:4][C:5]=2[O:19][CH2:20][CH2:21][CH3:22])=[N:9][C:10]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 136197376HCID 136197376, compound

Product 1

HCID 135890153HCID 135890153, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 2631-ButanolSolvent

Procedure

The compound of example 34 (200 mg, 0.55 mmol) was dissolved in n-butanol (10 ml), and added with glucose (200 mg, 1 mmol) and one drop of glacial acetic acid. The reaction mixture was heated under nitrogen protection to reflux for 12 h. The cooled reaction mixture was concentrated to dryness, and added with dichloromethane. The organic layer was washed with saturated saline (20 ml×3), dried with anhydrous Na2SO4, and concentrated under reduced pressure. The residue was passed through a silica gel column to give the title compound (60 mg, yield: 21%). 1H NMR (DMSO-d6) δ: 7.47 (1H, d), 7.21 (1H, dd), 7.09 (1H, d), 4.31 (1H, d), 4.01 (3H, t), 3.63 (1H, d), 3.46 (1H, d), 3.09-3.29 (4H, m), 2.57 (2H, q), 2.46 (2H, q), 1.72 (2H, m), 1.18 (6H, d), 0.95 (3H, t).

Workup

  1. temperatureThe reaction mixture was heated under nitrogen protection
  2. temperatureto reflux for 12 h
  3. customThe cooled reaction mixture
  4. concentrationwas concentrated to dryness
  5. additionadded with dichloromethane
  6. washThe organic layer was washed with saturated saline (20 ml×3)
  7. dry with materialdried with anhydrous Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d490473881b48d49ca7263a0010e5a5
Source dataset
uspto-grants-2014_10
Patent number
US08871777B2

Reaction notes

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