Reaktion #83090

ord-8f8b0776df724f59ab01c2e9a34d6605

Reaktionsgleichung

CC(C)(C)[Si](OC[C@H]1O[C@H](CI)C[C@H]1O)(c1ccccc1)c1ccccc1
product
CC(C)(C)[Si](OC[C@H]1O[C@H](CI)C[C@H]1O)(c1ccccc1)c1ccccc1
2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol
[Li+].[N-]=[N+]=[N-]
lithium azide
→
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
desired product
Ausbeute 96.5%
CC(C)(C)[Si](OC[C@H]1O[C@H](CN=[N+]=[N-])C[C@H]1O)(c1ccccc1)c1ccccc1
2,5-Anhydro-6-azido-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-D-arabino-hexitol
Ausbeute 96.5%

Edukte

CC(C)(C)[Si](OC[C@H]1O[C@H](CI)C[C@H]1O)(c1ccccc1)c1ccccc1
product
CC(C)(C)[Si](OC[C@H]1O[C@H](CI)C[C@H]1O)(c1ccccc1)c1ccccc1
2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol
[Li+].[N-]=[N+]=[N-]
lithium azide

Reagenzien

Keine

Lösungsmittel

O
water
CN(C)C=O
N,N-dimethylformamide

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITfollowed by room temperature for 18 hours
  2. 2
    Extraktionextracted with diethyl ether
  3. 3
    Einengenconcentrated in vacuo
  4. 4
    Sonstigepurified by chromatography (silica gel: 5-50% ethyl acetate/hexane)

Vorschrift

A solution, under argon, of 5.0 g of product from Example 275 in 10 ml of dry N,N-dimethylformamide is treated with 0.986 g of lithium azide. The minute is stirred at 80° C. for 1 hour followed by room temperature for 18 hours. The reaction is diluted with water, extracted with diethyl ether, concentrated in vacuo, purified by chromatography (silica gel: 5-50% ethyl acetate/hexane) to give 4.0 g of the desired product.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05623081uspto-grants-1997_04