Thiophenol → HCID 69789389, compound

HRID 353507Notes

Reaction equation

HRID 353507 reaction equation
[C:1]([C:4]([C@@:6]([C:20](=[O:22])[CH3:21])([C@:8]([C:17](=[O:19])[CH3:18])([C@H:10]([CH2:15][OH:16])[O:11][C:12](=[O:14])[CH3:13])[OH:9])[OH:7])=[O:5])(=O)[CH3:2].[C:23]1([SH:29])C=CC=C[CH:24]=1.Cl[Sn](Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:29]1[CH:23]=[CH:24][CH:2]=[C:1]1[C:4]([C@@:6]([C:20](=[O:22])[CH3:21])([C@:8]([C:17](=[O:19])[CH3:18])([C@H:10]([CH2:15][OH:16])[O:11][C:12](=[O:14])[CH3:13])[OH:9])[OH:7])=[O:5]

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 86587582HCID 86587582, compound

Product 1

HCID 69789389HCID 69789389, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Dry 1,2,3,4-O-tetraacetyl-L-arabinose (18.3 g, 57.5 mmol) was dissolved in dry CH2Cl2 (200 mL) and was cooled to −78° C. Thiophenol (6.5 mL, 63.3 mmol) was added followed by addition of SnCl4 (1M, 17.3 mL, 17.3 mmol). The reaction solution was stirred at −78° C. for 6 hours until the disappearance of the starting material in TLC. Saturated aqueous NaHCO3 (100 mL) was added. The organic layer was separated and the water layer was extracted with CH2Cl2 (30 mL) three times. The combined organic layer was washed with brine and dried over Na2SO4. The solvent was removed and the product was purified by silica gel column chromatography to afford thiophenyl-2,3,4-O-triacetyl-L-arabinose (16.95 g, 80%). Thiophenyl-2,3,4-O-triacetyl-L-arabinose (8.88 g, 24.1 mmol) was dissolved in MeOH (120 mL) followed by the addition of sodium methoxide (65 mg, 2 mmol ). The reaction solution was stirred at 25° C. for three hours, then saturated aqueous NH4Cl was added. The organic layer was separated and the water layer was extracted with CH2Cl2 (30 mL) three times. The combined organic layer was washed with brine and dried over Na2SO4. The solvent was removed and the product was purified by silica gel column chromatography to afford 22 (5.53 g, 22.9 mmol, 95%)

Workup

  1. customThe organic layer was separated
  2. extractionthe water layer was extracted with CH2Cl2 (30 mL) three times
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bbed2d1ab4694fcabc4145493e8b08c6
Source dataset
uspto-grants-2004_06
Patent number
US06753414B2

Reaction notes

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