m-Chloroperbenzoic acid → HCID 15460411, compound

HRID 1637423Notes

Reaction equation

HRID 1637423 reaction equation
[N:1]([C@@H:4]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH3:26])[O:14][C@H:6]([S:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@H:5]1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[N+:2]=[N-:3].C1C=C(Cl)C=C(C(OO)=[O:45])C=1>C(Cl)Cl>[N:1]([C@@H:4]1[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@H:15]([CH3:26])[O:14][C@H:6]([S:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:45])[C@H:5]1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 21967604HCID 21967604, compound

Product 1

HCID 15460411HCID 15460411, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-20 °C

Procedure

To a solution of phenyl 3-azido-4-O-benzoyl-3,6-di-deoxy-2-O-(4-methoxybenzyl)-1-thio-β-L-galactopyranoside (β-16, prepared above), (350 mg, 0.7 mmol) in 10 mL of CH2Cl2 at -78° C. is added a solution of mCPBA (170 mg, 1.1 mmol) in 2 mL of CH2Cl2. The reaction mixture is allowed to warm to -20° C. and then quenched with TEA (500 μL, 3.59 mmol). The reaction mixture is diluted with 10 mL of CH2Cl2, washed with saturated NaHS3 (10 mL), saturated NaHCO3 (10 mL), dried over Na2SO4, filtered and concentrated. The crude product is purified by flash chromatography (EtOAc/petroleum ether) to give the title compound as a mixture of diastereomers.

Workup

  1. washwashed with saturated NaHS3 (10 mL), saturated NaHCO3 (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product is purified by flash chromatography (EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-af1fedfd1e274a45b26489becc9c30a2
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Reaction notes

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