3β-cholestanyl trimethylsilyl ether | 42995-55-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-cholestanyl trimethylsilyl ether
• 英文别名: Dihydrocholesterol-trimethylsilyl-ether；[(3S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy-trimethylsilane
• CAS: 42995-55-1
• 化学式: C₃₀H₅₆OSi
• 分子量: 460.86
• InChiKey: HRLPEXVPNOBUDF-SGCSJPMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.33
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,5-三-O-(苯基甲基)-D-呋喃核糖 、 3β-cholestanyl trimethylsilyl ether 在 三氟甲磺酸酐 、 diphenyltin sulfide 、 cesium fluoride 作用下， 以 乙醚 为溶剂， 以95%的产率得到3β-cholestanyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside
  参考文献：
  名称：

  Mukaiyama, Teruaki; Matsubara, Koki; Suda, Shinji, Chemistry Letters, 1991, # 6, p. 981 - 984

  摘要：

  DOI：

文献信息

• A Novel Glycosylation Reaction of 2-Amino-2-deoxy-D-glucopyranose Using Dimethylphosphinothioate
  作者：Toshiyuki Inazu、Takashi Yamanoi

  DOI：10.1246/cl.1989.69

  日期：1989.1

  β-Glucosides were stereoselectively obtained in good yields from 3,4,6-tri-O-benzyl-2-benzyloxycarbonylamino-2-deoxy-α-d-glucopyranosyl dimethylphosphinothioate with several alcohols in the presence of iodine and a catalytic amount of trityl or perchlorate salts.

  在碘和催化量的三苯甲基盐或高氯酸盐存在下，3,4,6-三-O-苄基-2-苄氧羰基氨基-2-脱氧-α-d-吡喃葡萄糖基二甲基硫代磷酸酯与几种醇立体选择性地获得了 β-葡萄糖苷，收率很高。
• Catalytic Stereoselective Synthesis of 2-Amino-2-Deoxy-α-D-Glucopyranosides and Galactopyranosides
  作者：Koki Matsubara、Teruaki Mukaiyama

  DOI：10.1246/cl.1993.2145

  日期：1993.12

  In the presence of a catalyst generated from SnCl4 and a silver salt, various 2-amino-2-deoxy-α-D-glucopyranosides or galactopyranosides are stereoselectively synthesized in good yields with high stereoselectivities through anomerization step starting from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose or galactopyranose and alkyl trimethylsilyl ethers, respectively.

  在 SnCl4 和银盐生成的催化剂存在下，通过从 1,3,4 开始的异构化步骤，立体选择性地以良好的产率和高立体选择性合成了各种 2-氨基-2-脱氧-α-D-吡喃葡萄糖苷或吡喃半乳糖苷，分别为6-四-O-乙酰基-2-脱氧-2-(2,2,2-三氯乙氧基羰基氨基)-β-D-吡喃葡萄糖或吡喃半乳糖和烷基三甲基甲硅烷基醚。
• Stereoselective Synthesis of 1,2-cis-Arabinofuranosides Using a New Titanium Catalyst
  作者：Teruaki Mukaiyama、Masaaki Yamada、Shinji Suda、Yoshihiro Yokomizo、Shu Kobayashi

  DOI：10.1246/cl.1992.1401

  日期：1992.8

  In the presence of catalytic amounts of [1,2-benzenediolato(2-)-O,O′]oxotitanium and trimethylsilyl triflate, 1-O-trimethylsilyl-2,3,5-tri-O-benzyl-D-arabinofuranose stereoselectively reacts with various trimethylsilyl ethers to afford the corresponding 1,2-cis-arabinofuranosides in high yields.

  在催化量的[1,2-苯二酚(2-)-O,O']氧钛和三氟甲磺酸三甲基硅酯存在下，立体选择性地生成1-O-三甲基硅基-2,3,5-三-O-苄基-D-阿拉伯呋喃糖与各种三甲基甲硅烷基醚反应，以高产率得到相应的 1,2-顺式-阿拉伯呋喃糖苷。
• Catalytic Stereoselective Synthesis of α- or β-Glucosides Using a Single Glycosyl Donor, 1-O-2′-(2′-Methoxyethoxy)acetyl-Glucopyranose Derivative
  作者：Koki Matsubara、Takenori Sasaki、Teruaki Mukaiyama

  DOI：10.1246/cl.1993.1373

  日期：1993.8

  In the presence of a catalytic amount of active acidic species generated from SnCl4 and AgClO4, various α-glucosides are stereoselectively synthesized in excellent yields from 1-O-2′-(2′-methoxyethoxy)acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose and alkyl trimethylsilyl ethers. β-Glucosides are also selectively prepared by using a catalyst, generated from SiCl4 and AgClO4 in the above reaction.

  在 SnCl4 和 AgClO4 产生的催化量的活性酸性物质存在下，可以从 1-O-2'-(2'-甲氧基乙氧基)乙酰基-2,3,4,6 立体选择性地合成各种 α-葡萄糖苷，收率优异-四-O-苄基-D-吡喃葡萄糖和烷基三甲基甲硅烷基醚。 β-葡萄糖苷也可以通过使用上述反应中由SiCl4和AgClO4产生的催化剂选择性地制备。
• A Highly Stereoselective Synthesis of α-Glucosides from 1-<i>O</i>-Acetyl Glucose by Use of Tin(IV) Chloride–Silver Perchlorate Catalyst System
  作者：Teruaki Mukaiyama、Tohru Takashima、Manabu Katsurada、Hiroyuki Aizawa

  DOI：10.1246/cl.1991.533

  日期：1991.4

  In the presence of a catalytic amount of tin(IV) species generated from tin(IV) chloride and silver perchlorate, 1-O-acetyl-d-glucose stereoselectively reacts with silyl alkoxides to give the corresponding α-glucosides in high yields.

  在氯化亚锡和过氯酸银生成的催化量的四价锡物种存在下，1-O-乙酰基-D-葡萄糖与硅烷醇盐发生立体选择性反应，生成相应的α-葡萄糖苷，且收率很高。