Triacetoxyperiodinane → HCID 59013442, compound

HRID 1716975Notes

Reaction equation

HRID 1716975 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:54]=[CH:53][C:52]([CH2:55][CH3:56])=[CH:51][CH:50]=3)[CH:46]=1)[CH:41]([OH:58])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@@H:12]([CH2:31][O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][C@:10]21[C:47]1[C:42](=[CH:43][C:44]([Cl:57])=[C:45]([CH2:48][C:49]3[CH:50]=[CH:51][C:52]([CH2:55][CH3:56])=[CH:53][CH:54]=3)[CH:46]=1)[C:41](=[O:58])[CH2:40]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59013481HCID 59013481, compound

Product 1

HCID 59013442HCID 59013442, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0° C. solution of (1S,3′R,4′S,5′R,6′R)-3′,4′,5′-tris(benzyloxy)-6′-(benzyloxymethyl)-5-chloro-6-(4-ethylbenzyl)-2,3,3′,4′,5′,6′-hexahydrospiro[indene-1,2′-pyran]-3-ol (40 mg, 0.05 mmol) in dry dichloromethane (1.0 mL) was added dropwise a solution of Dess-Martin reagent (43 mg, 0.1 mmol) in 0.5 mL of dry dichloromethane. The reaction mixture was stirred for 3.5 h at room temperature and quenched by addition of 2 mL of 1 M aqueous NaOH solution when TLC showed the reaction was complete. The organic layer was separated and the aqueous layer was extracted 2× with CH2Cl2 (10 mL). The combined organic layers were washed 1× with NaHSO3 (10 mL), 2× with NaHCO3 (10 mL), 3× with brine (10 mL) prior to drying over anhydrous Na2SO4. Concentration under reduced pressure and purification of the crude product by preparative TLC provided 36 mg of the pure product.

Workup

  1. customquenched by addition of 2 mL of 1 M aqueous NaOH solution when TLC
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted 2× with CH2Cl2 (10 mL)
  4. washThe combined organic layers were washed 1× with NaHSO3 (10 mL), 2× with NaHCO3 (10 mL), 3× with brine (10 mL)
  5. dry with materialto drying over anhydrous Na2SO4
  6. concentrationConcentration
  7. customunder reduced pressure and purification of the crude product by preparative TLC

Sources & evidence

ORD record
ord-9fbef5d9271540f3be7e18e5f72f72de
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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