ethyl 2-O-(3,5-difluorobenzensulfonyl)-α-D-thioglucopyranoside | 1399292-86-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-(3,5-difluorobenzensulfonyl)-α-D-thioglucopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-2-ethylsulfanyl-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 3,5-difluorobenzenesulfonate
• CAS: 1399292-86-4
• 化学式: C₁₄H₁₈F₂O₇S₂
• 分子量: 400.422
• InChiKey: OQYLKEOQWSROCY-RKQHYHRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  147
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,5-二氟苯磺酰氯 、 (2R,3R,4S,5S,6R)-2-Ethylsulfanyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 在 二丁基二氯化锡 、 1,2,2,6,6-五甲基哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 12.17h， 以95%的产率得到ethyl 2-O-(3,5-difluorobenzensulfonyl)-α-D-thioglucopyranoside
  参考文献：
  名称：

  Chemo- and Regioselective Monosulfonylation of Nonprotected Carbohydrates Catalyzed by Organotin Dichloride under Mild Conditions

  摘要：

  The catalytic regioselective monosulfonylation of nonprotected carbohydrates using organotin dichloride under mild conditions is examined. The carbohydrates were chemo- and regioselectively converted to the corresponding monosulfonates in the presence of monoalcohols using catalytic dibutyltin dichloride. The regioselectivity of the sulfonylation is attributed to the intrinsic character of the carbohydrates derived from the relative stereochemistry between their hydroxy groups.

  DOI：

  10.1021/jo301353k

文献信息

• Chemo- and Regioselective Monosulfonylation of Nonprotected Carbohydrates Catalyzed by Organotin Dichloride under Mild Conditions
  作者：Wataru Muramatsu

  DOI：10.1021/jo301353k

  日期：2012.9.21

  The catalytic regioselective monosulfonylation of nonprotected carbohydrates using organotin dichloride under mild conditions is examined. The carbohydrates were chemo- and regioselectively converted to the corresponding monosulfonates in the presence of monoalcohols using catalytic dibutyltin dichloride. The regioselectivity of the sulfonylation is attributed to the intrinsic character of the carbohydrates derived from the relative stereochemistry between their hydroxy groups.