반응 #83089

ord-1a708cdcea0c474cb7bb1ece0126d881

반응 방정식

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
수율 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
수율 76.3%

반응물

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

시약

없음

용매

CCOCC.O
diethyl ether water

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

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

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05623081uspto-grants-1997_04