Triacetoxyperiodinane → HCID 57857023, compound

HRID 561754Notes

Reaction equation

HRID 561754 reaction equation
[S:1]1[C:5]([C@H:6]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[CH2:12][C@H:11]([OH:21])[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[S:1]1[C:5]([C@H:6]([O:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][O:33]2)/[CH:7]=[CH:8]/[C@H:9]2[C@H:13]([O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][O:16]3)[CH2:12][C:11](=[O:21])[C@@H:10]2[CH2:22]/[CH:23]=[CH:24]\[CH2:25][CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[CH:4][C:3]2[CH:38]=[CH:39][CH:40]=[CH:41][C:2]1=2

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57857015HCID 57857015, compound2×

Product 1

HCID 57857023HCID 57857023, compoundYield 109.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution consisting of (Z)-7-((1R,2R,3R,5S)-2-((3R,E)-3-(benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)cyclopentyl)hept-5-enoic acid (intermediate 32, 0.191 g, 0.327 mmol) in anhydrous DCM (3 mL) was added Dess-Martin periodinane (0.153, 0.360 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was concentrated under reduced pressure and purified on an 8-g Analogix flash silica cartridge. Elution with 200:1 DCM-methanol with 0.5% acetic acid (300 mL) afforded the title intermediate 33 (208 mg); MS (+cAPCI) m/z 605 (m+Na+).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified on an 8-g Analogix flash silica cartridge
  3. washElution with 200:1 DCM-methanol with 0.5% acetic acid (300 mL)

Sources & evidence

ORD record
ord-09d0f5d9e4ee4444b23af2fce85199d9
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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