methyl 3-O-[3,5-bis(trifluoromethyl)benzenesulfonyl]-α-D-mannopyranoside | 1422662-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-[3,5-bis(trifluoromethyl)benzenesulfonyl]-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl] 3,5-bis(trifluoromethyl)benzenesulfonate
• CAS: 1422662-85-8
• 化学式: C₁₅H₁₆F₆O₈S
• 分子量: 470.344
• InChiKey: ILLYZHHJBBIOQK-BNDIWNMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  3,5-二三氟甲基苯磺酰氯 、 甲基-D-丙噻 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98%的产率得到methyl 3-O-[3,5-bis(trifluoromethyl)benzenesulfonyl]-α-D-mannopyranoside
  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

• Selectivity Switch in the Catalytic Functionalization of Nonprotected Carbohydrates: Selective Synthesis in the Presence of Anomeric and Structurally Similar Carbohydrates under Mild Conditions
  作者：Wataru Muramatsu、Yuki Takemoto

  DOI：10.1021/jo3024279

  日期：2013.3.15

  A catalytic process for the chemo- and regioselective functionalization of nonprotected carbohydrates has been developed. This novel process allows selective thiocarbonylation, acylation, and sulfonylation of a particular hydroxy group in a particular carbohydrate in the simultaneous presence of structurally similar carbohydrates such as anomers. In addition, the chemoselectivity can be switched by regulating only the length of the alkyl chain in the organotin catalyst.
• 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.