反応 #83104

ord-65cba0136c614283a20f8a7670d3a412

反応方程式

Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](C)C[C@@H]2O)cc1
product
Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](C)C[C@@H]2O)cc1
2,5-Anhydro-1,3-dideoxy-D-ribo-hexitol 6-(4-Methylbenzenesulfonate)
CN(C)C=O
N,N-dimethylformamide
[N-]=[N+]=[N-].[Na+]
sodium azide
→
C[C@H]1C[C@H](O)[C@@H](CN=[N+]=[N-])O1
desired product
収率 77.4%
C[C@H]1C[C@H](O)[C@@H](CN=[N+]=[N-])O1
2,5-Anhydro-6-azido-1,3,6-trideoxy-D-ribo-hexitol
収率 77.4%

反応物

Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](C)C[C@@H]2O)cc1
product
Cc1ccc(S(=O)(=O)OC[C@H]2O[C@@H](C)C[C@@H]2O)cc1
2,5-Anhydro-1,3-dideoxy-D-ribo-hexitol 6-(4-Methylbenzenesulfonate)
CN(C)C=O
N,N-dimethylformamide
[N-]=[N+]=[N-].[Na+]
sodium azide

試薬

なし

溶媒

CCOCC
diethyl ether

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    洗浄washed with water and saturated sodium chloride
  2. 2
    その他dried
  3. 3
    濃縮concentrated in vacuo

実験手順

A mixture, under argon, of 0.560 g of product from Example 337, 2 ml of N,N-dimethylformamide and 0.250 g of sodium azide is stirred at 75° C. for 12 hours. The reaction mixture is diluted with diethyl ether, washed with water and saturated sodium chloride, dried and concentrated in vacuo to give 0.238 g of the desired product.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05623081uspto-grants-1997_04