Triacetoxyperiodinane → HCID 69082386, compound

HRID 1396250Notes

Reaction equation

HRID 1396250 reaction equation
[CH3:1][N:2]([CH3:35])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([CH:12]([OH:14])[CH3:13])[C@@H:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[C@H:8]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:6]2[N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH3:35][N:2]([CH3:1])[C:3]1[S:4][C@H:5]2[O:11][C@H:10]([C:12](=[O:14])[CH3:13])[C@@H:9]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[C@H:8]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=3)[C@H:6]2[N:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69082443HCID 69082443, compound

Product 1

HCID 69082386HCID 69082386, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-((3aR,5R,6S,7R,7aR)-2-(dimethylamino)-6,7-bis(4-methoxybenzyloxy)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)ethanol (450 mg, 0.90 mmol, mixture of diastereomers, faster eluting isomer: slower eluting isomer 1:5 by HPLC and 1HNMR) in dichloromethane (20 mL) was treated with Dess-Martin reagent (760 mg, 1.80 mmol) for 2 hours at room temperature. The reaction mixture was quenched by sat. aqueous Na2S2O3 solution (20 mL) and sat. aqueous NaHCO3 solution (20 mL), and extracted with dichloromethane (2×20 mL). The combined, organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue, which was purified by silica gel column, eluted with 2-3% methanol in dichloromethane to give compound 33 as a yellow syrup (400 mg, 88%). (ES, m/z): [M+H]+ 501.0; 1H NMR (300 MHz, CDCl3) δ 7.25-7.30 (m, 4H), 6.83-6.90 (m, 4H), 6.29-6.31 (d, J=6.0 Hz, 1H), 4.26-4.64 (m, 6H), 3.81-3.98 (m, 8H), 2.96-3.02 (m, 6H), 2.17 (s, 3H).

Workup

  1. customThe reaction mixture was quenched by sat. aqueous Na2S2O3 solution (20 mL) and sat. aqueous NaHCO3 solution (20 mL)
  2. extractionextracted with dichloromethane (2×20 mL)
  3. dry with materialorganic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide a residue, which
  6. customwas purified by silica gel column
  7. washeluted with 2-3% methanol in dichloromethane

Sources & evidence

ORD record
ord-81c341bb3f2c413bacefe432c6b638d7
Source dataset
uspto-grants-2014_12
Patent number
US08901087B2

Reaction notes

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