Reaktion #83089

ord-1a708cdcea0c474cb7bb1ece0126d881

Reaktionsgleichung

C=CCC(O)C(O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
product
C=CCC(O)C(O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol
O=C([O-])O.[Na+]
sodium bicarbonate
II
iodine
→
CC(C)(C)[Si](OC[C@H]1O[C@H](CI)C[C@H]1O)(c1ccccc1)c1ccccc1
desired product
Ausbeute 76.3%
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
Ausbeute 76.3%

Edukte

C=CCC(O)C(O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
product
C=CCC(O)C(O)CO[Si](c1ccccc1)(c1ccccc1)C(C)(C)C
1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol
O=C([O-])O.[Na+]
sodium bicarbonate
II
iodine

Reagenzien

Keine

Lösungsmittel

CCOCC.O
diethyl ether water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigequenched with 15 ml of saturated sodium sulfite
  2. 2
    workup.ADDITIONdiluted with 100 ml of water
  3. 3
    Extraktionthe reaction minute is extracted with diethyl ether
  4. 4
    Sonstigedried
  5. 5
    Einengenconcentrated in vacuo
  6. 6
    Sonstigepurified by chromatography (silica gel: 0-10% ethyl acetate/hexane)

Vorschrift

A 0° C. solution of 14.67 g of product from Example 274 in 200 ml of 3:1 diethyl ether/water is treated with 4.99 g of sodium bicarbonate and 15.07 g of iodine. The reaction minute is stirred vigorously for 24 hours at room temperature, quenched with 15 ml of saturated sodium sulfite, and diluted with 100 ml of water. the reaction minute is extracted with diethyl ether, dried, concentrated in vacuo, and purified by chromatography (silica gel: 0-10% ethyl acetate/hexane) to give 15.0 g of the desired product.

Quelle

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