2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside | 1185741-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
• CAS: 1185741-87-0
• 化学式: C₂₃H₃₂O₇S
• 分子量: 452.569
• InChiKey: HKHWNTSKZKMTPQ-OYXYZOQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  31.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以98%的产率得到2-methyl-5-tert-butylphenyl 1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis

  摘要：

  The first synthesis of two natural triterpenoid saponins, which were isolated from the roots of Pulsatilla chinensis and exhibited excellent in vitro cytotoxic activity against HL-60 cells, was concisely achieved in a convergent approach. We employed an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and trichloroacetimidate donors in one-pot reaction as a key step. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.05.011
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 、 5-叔丁基-2-甲基苯硫酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Concise synthesis of two natural triterpenoid saponins, oleanolic acid derivatives isolated from the roots of Pulsatilla chinensis

  摘要：

  The first synthesis of two natural triterpenoid saponins, which were isolated from the roots of Pulsatilla chinensis and exhibited excellent in vitro cytotoxic activity against HL-60 cells, was concisely achieved in a convergent approach. We employed an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and trichloroacetimidate donors in one-pot reaction as a key step. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.carres.2009.05.011

文献信息

• Synthetic studies toward the anthrax tetrasaccharide: alternative synthesis of this antigen
  作者：Ophélie Milhomme、Sandrine G.Y. Dhénin、Florence Djedaïni-Pilard、Vincent Moreau、Cyrille Grandjean

  DOI：10.1016/j.carres.2012.01.007

  日期：2012.7

  conjugation, has been envisaged by both [2+2] and [1+3] approaches from D-fucose and L-rhamnose. The successful route reported herein relies on a [1+3] strategy in which the 1,2-trans-glycosidic linkages have been secured using a participating group at the 2-position of the donors using conventional thio as well as trichloroacetimidate glycosylation chemistry. The exchange of the ester to benzyl protective

  D-岩藻糖和L-鼠李糖的[2 + 2]和[1 + 3]方法都可以合成适于结合的炭疽四糖。本文报道的成功途径依赖于[1 + 3]策略，其中1,2-反式-糖苷键已通过使用常规硫代以及三氯乙酰亚氨酸酯糖基化化学方法在供体的2位使用参与基团得到固定。酯与鼠李糖基部分上的苄基保护基的交换是实现四糖最终组装和功能化的关键。