Sodium Azide → HCID 10978032, compound

HRID 461539Notes

Reaction equation

HRID 461539 reaction equation
[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15]OS(C2C=CC(C)=CC=2)(=O)=O)[O:8][CH:7]=[CH:6]1)(=[O:3])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)P(N(C)C)(N(C)C)=O>[C:1]([O:4][C@H:5]1[C@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@@H:9]([CH2:15][N:27]=[N+:28]=[N-:29])[O:8][CH:7]=[CH:6]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 11280564HCID 11280564, compound

Product 1

HCID 10978032HCID 10978032, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

3,4-Di-O-acetyl-1,2-dideoxy-6-O-tosyl-D-arabinohex-1-enopyranose (50g.) was dissolved in hexamethylphosphoramide (800 ml.) and sodium azide (34 g.) was added and the solution was stirred at 25° for 24 hours. The hexamethylphosphoramide was distilled off under high vacuum and the residue was taken up in chloroform and washed with water. The chloroform extract was dried (MgSO4), filtered and evaporated to give a crude gum which was chromatographed on a silica gel column (150 × 7.5 cm.) using 7% acetone in hexane as the eluent to give 3,4-di-O-acetyl-6-azido-1,2,6-trideoxy-D-arabinohex-1-enopyranose (25 g.) as a colorless gum, (Found: C, 47.23; H, 5.30; N, 16.37. C10N13N3O5 requires: C, 47.06; H, 5.13; N, 16.46%), [α]D26 × 25.1° (CH3OH), νmax (CHCl3) 2110, 1755, 1660, 1220, 1040 cm. -1, δ(CDCl3) 2.06, 2.09 (6H, s, OAc), 4.91 (1H, ddd, J = 6.5Hz, 3.0Hz, 1Hz, H2), and 6.53 ppm. (1H, dd, J = 6.5Hz, 1.5Hz, H1).

Workup

  1. distillationThe hexamethylphosphoramide was distilled off under high vacuum
  2. washwashed with water
  3. extractionThe chloroform extract
  4. dry with materialwas dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give a crude gum which
  8. customwas chromatographed on a silica gel column (150 × 7.5 cm.)

Sources & evidence

ORD record
ord-ff5e35ffc2894a15b7037b6588a48866
Source dataset
uspto-grants-1977_12
Patent number
US04063015

Reaction notes

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