反応 #83089

反応方程式

product

1-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-5-hexene-2,3-diol

sodium bicarbonate

iodine

→

desired product

収率 76.3%

2,5-Anhydro-4,6-dideoxy-1-O-[(1,1-dimethylethyl)diphenylsilyl]-6-iodo-D-arabino-hexitol

収率 76.3%

溶媒

diethyl ether water

反応条件

後処理

1. 1
   その他quenched with 15 ml of saturated sodium sulfite
2. 2
   workup.ADDITIONdiluted with 100 ml of water
3. 3
   抽出the reaction minute is extracted with diethyl ether
4. 4
   その他dried
5. 5
   濃縮concentrated in vacuo
6. 6
   その他purified by chromatography (silica gel: 0-10% ethyl acetate/hexane)

実験手順

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.

出典