Triacetoxyperiodinane → HCID 57867404, compound

HRID 1516254Notes

Reaction equation

HRID 1516254 reaction equation
[Si:1]([O:18][CH2:19][C@@H:20]1[C@@H:24]([OH:25])[C@:23]([F:27])([CH3:26])[CH:22]([O:28][CH3:29])[O:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[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>[Si:1]([O:18][CH2:19][C@@H:20]1[C:24](=[O:25])[C@:23]([F:27])([CH3:26])[CH:22]([O:28][CH3:29])[O:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57867368HCID 57867368, compound

Product 1

HCID 57867404HCID 57867404, compoundYield 150.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,3R,4R)-2-((tert-butyldiphenylsilyloxy)methyl)-4-fluoro-5-methoxy-4-methyl-tetrahydrofuran-3-ol (about 16 g, 38.2 mmol) and Dess-Martin periodinane (about 24.3 g, 57.4 mmol) in dichloromethane (about 150 ml) stirred at about 0° C. to room temperature under Nitrogen atmosphere. Completion of the reaction monitored by thin-layer chromatography and quenched by the saturated solution of sodium sulphate and sodium bicarbonate in equal volumes (100 ml+100 ml). The aqueous layers were extracted with dichloromethane and the combined organic extracts were washed with water, brine and dried over sodium sulphate and concentrated under reduced pressure to yield the title compound (24 g as crude). 1H NMR (300 MHz, CDCl3): δ 7.69-7.67 (m, 4H), 7.42-7.39 (m, 6H), 5.07 (d, 1H, J=12.3 Hz), 4.38 (dd, 1H, J=5.1 Hz, 3.3 Hz), 3.889-3.83 (m, 2H), 3.46 (s, 3H), 1.42 (d, 3H, J=24 Hz), 1.03 (s, 9H); Mass: [M+Na]+: 439 (65%); IR cm−: 2934, 2859, 1783, 1382, 1114, 998, 703.

Workup

  1. customquenched by the saturated solution of sodium sulphate and sodium bicarbonate in equal volumes (100 ml+100 ml)
  2. extractionThe aqueous layers were extracted with dichloromethane
  3. washthe combined organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7c042409c72f44709080d05cf6030a07
Source dataset
uspto-grants-2012_07
Patent number
US08227431B2

Reaction notes

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