Реакция #83089

ord-1a708cdcea0c474cb7bb1ece0126d881

Уравнение реакции

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
Выход 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
Выход 76.3%

Реактанты

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

Реагенты

Нет

Растворители

CCOCC.O
diethyl ether water

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

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

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05623081uspto-grants-1997_04