Diethyl Ether → HCID 22808782, compound

HRID 461540Notes

Reaction equation

HRID 461540 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([CH2:11]OS(C2C=CC(C)=CC=2)(=O)=O)[O:9][CH:8]=[CH:7][CH2:6]1)(=[O:3])[CH3:2].[N-:23]=[N+:24]=[N-:25].[Na+].CCOCC>CN(C)P(N(C)C)(N(C)C)=O>[C:1]([O:4][C@@H:5]1[C@@H:10]([CH2:11][N:23]=[N+:24]=[N-:25])[O:9][CH:8]=[CH:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 14392886HCID 14392886, compound

Product 1

HCID 22808782HCID 22808782, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

4-O-Acetyl-3-deoxy-6-O-tosyl-D-glucal (550 mg.) and sodium azide (550 mg.) were dissolved in hexamethylphosphoramide (50 ml.) and the mixture was stirred at 25° for 24 hours. The reaction mixture was poured into ether and extracted with water and the ether extract was dried (MgSO4) and evaporated and the product was chromatographed on a silica gel column (58 × 2.5 cm) using 7% acetone in hexane as the eluent to give 4-O-acetyl-6-azido-3,6-dideoxy-D-glucal (200 mg.) as a colorless oil, (Found: C, 48.84; H, 5.33; N,21.49. C8H11N3O3 requires: C, 48.72; H, 5.62; N, 21.31%), [α]D26 = 158.8° (CH3OH), νmax (film) 2100, 1720, 1660, 1220, 1050 cm.-1, δ(CDCl3) 2.09 (3H, s, OAc), 4.72 (1H, ddd, H = 6Hz, J = 4.5Hz, J = 3Hz, H2) and 6.39 ppm (1H, ddd, J = 2Hz, J = H1. )

Workup

  1. extractionextracted with water
  2. extractionthe ether extract
  3. dry with materialwas dried (MgSO4)
  4. customevaporated
  5. customthe product was chromatographed on a silica gel column (58 × 2.5 cm)

Sources & evidence

ORD record
ord-2c7f6c5c6cff498885881e827025b78e
Source dataset
uspto-grants-1977_12
Patent number
US04063015

Reaction notes

Loading…