Sodium Iodide → HCID 13316985, compound

HRID 1719627Notes

Reaction equation

HRID 1719627 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:16][C@@H:15]([CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[O:14][C@H:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:29].[Na+]>CC(C)=O.OP(O)=O.O[Mo](O)(=O)=O>[CH2:1]([O:8][C@@H:9]1[CH2:16][C@@H:15]([CH2:17][I:29])[O:14][C@H:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 86740302HCID 86740302, compound

Product 1

HCID 13316985HCID 13316985, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 21863154Dihydroxy(dioxo)molybdenum;phosphonic acidCatalystHCID 180AcetoneSolvent

Procedure

Methyl 3-O-benzyl-6-O-tosyl-2,4-dideoxy-α-D-erythro-hexopyranoside (3.0 g; 7.34 mmoles) and sodium iodide (13 g; 86.7 mmoles) are dissolved in acetone (130 ml). The resulting solution is refluxed under nitrogen and protected from the light for 24 hours. When tlc shows the reaction is complete (fluorosilica-methylene chloride, visualization with phosphomolybdic acid and heat), the acetone is evaporated in vacuo. The residue is partitioned between ether and water. The ether layer is washed with dilute aqueous sodium thiosulfate, then twice with water, dried (MgSO4), filtered, and the solvent is evaporated in vacuo to give crude product which is purified by flash chromatography on silica gel on a 60 mm×150 mm column. Elution with methylene chloride gives 2.0 g of methyl 3-O-benzyl-6-iodo-2,4,6-trideoxy-α-D-erythro-hexopyranoside. [α]D24 +53.45 (c, 0.66 CHCl3). Pmr (300 MHz) (DCCl3) δ1.52 (1H, m); 1.75 (1H, m); 1.95 (1H, m) 2.02 (1H, m); 3.21 (2H, m); 3.47 (3H, s); 3.78 (1H, m) 4.10 (1H, m); 4.56 (2H, q); 4.81 (1H, d); 7.24-7.42 (5H, m).

Workup

  1. temperatureThe resulting solution is refluxed under nitrogen
  2. customthe acetone is evaporated in vacuo
  3. customThe residue is partitioned between ether and water
  4. washThe ether layer is washed with dilute aqueous sodium thiosulfate
  5. dry with materialtwice with water, dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated in vacuo
  8. customto give crude product which
  9. customis purified by flash chromatography on silica gel on a 60 mm×150 mm column
  10. washElution with methylene chloride

Sources & evidence

ORD record
ord-e20d084e34a74f0b8e5afbc337d3b8fb
Source dataset
uspto-grants-1985_09
Patent number
US04540796

Reaction notes

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