Triacetoxyperiodinane → HCID 66885708, compound

HRID 2204052Notes

Reaction equation

HRID 2204052 reaction equation
[CH2:1]([O:4][C@@H:5]1[C@@H:10]([O:11][CH2:12][CH:13]=[CH2:14])[C@H:9]([O:15][CH2:16][CH:17]=[CH2:18])[C@@H:8]([CH2:19][O:20][CH2:21][CH:22]=[CH2:23])[O:7][C:6]1([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH2:40][CH3:41])=[CH:35][CH:34]=2)[CH:26]=1)[OH:24])[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:4][C@H:5]([C@@H:10]([O:11][CH2:12][CH:13]=[CH2:14])[C@H:9]([O:15][CH2:16][CH:17]=[CH2:18])[C:8](=[O:7])[CH2:19][O:20][CH2:21][CH:22]=[CH2:23])[C:6]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([O:39][CH2:40][CH3:41])=[CH:37][CH:38]=2)[CH:26]=1)=[O:24])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 53628871HCID 53628871, compound

Product 1

HCID 66885708HCID 66885708, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound from Step D (0.93 g, 1.59 mmol) in CH2Cl2 (25 ml) was added Dess-Martin periodinane (0.68 g, 1.59 mmol). The mixture was stirred at room temperature for 1 hour and then a second portion of Dess-Martin periodinane (1 eqiv.) was added. Stirring was continued for another hour and then the reaction was quenched with 1NNaOH (˜4 ml). H2O was added and the organic layer separated. The aqueous layer was back extracted with CH2Cl2, dried and concentrated to give a yellow waxy solid. Purification by silica gel chromatography (15%-20% EtOAc/hexanes) afforded (2R,3R,4S)-2,3,4,6-tetrakis-allyloxy-1-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-hexane-1,5-dione (0.60 g, 1.03 mmol, 65%) as a white solid. MS (ES+) [M+NH4]+=600.

Workup

  1. stirringStirring
  2. waitwas continued for another hour
  3. customthe reaction was quenched with 1NNaOH (˜4 ml)
  4. additionH2O was added
  5. customthe organic layer separated
  6. extractionThe aqueous layer was back extracted with CH2Cl2
  7. customdried
  8. concentrationconcentrated
  9. customto give a yellow waxy solid
  10. customPurification by silica gel chromatography (15%-20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d7cc9a186a294493985aac0679859d3a
Source dataset
uspto-grants-2016_06
Patent number
US09365602B2

Reaction notes

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