methyl (2S)-2-(phenylmethoxycarbonylamino)-3-trimethylsilyloxypropanoate | 135195-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-(phenylmethoxycarbonylamino)-3-trimethylsilyloxypropanoate
• CAS: 135195-50-5
• 化学式: C₁₅H₂₃NO₅Si
• 分子量: 325.437
• InChiKey: WVDDBAKRSKZDJC-ZDUSSCGKSA-N

物化性质

• 沸点：
  402.6±45.0 °C(Predicted)
• 密度：
  1.099±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-(phenylmethoxycarbonylamino)-3-trimethylsilyloxypropanoate 、 1-O-acetyl-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose 在 甲基三氯硅烷 、 silver perchlorate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 以85%的产率得到[(2R,3R,4S,5R,6R)-3,4,5-tris(2,2-dimethylpropanoyloxy)-6-[(2S)-3-methoxy-3-oxo-2-(phenylmethoxycarbonylamino)propoxy]oxan-2-yl]methyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount of Active Species Generated from Methyltrichlorosilane and Silver Perchlorate

  摘要：

  利用由 MeSiCl3 和 AgClO4 生成的活性物质，从五乙酰吡喃葡萄糖和烷基硅基醚开始，进行了高效的 β-糖基化催化反应。在邻位效应的帮助下，1-O-乙酰基-2,3,4,6-四-O-特戊酰基-β-D-吡喃葡萄糖与烷基硅醚发生了立体选择性反应，以高产率得到了相应的β-葡糖苷。

  DOI：

  10.1246/cl.1992.2105

文献信息

• An Efficient Method for the Stereoselective Synthesis of<i>β</i>-D- and<i>α</i>-D-Ribofuranosides from 2,3,5-Tri-<i>O</i>-benzyl-D-ribofuranose by the Use of [Catecholato(2−)-<i>O</i>,<i>O</i>′]oxotitanium and Trifluoromethanesulfonic Anhydride
  作者：Shinji Suda、Teruaki Mukaiyama

  DOI：10.1246/bcsj.66.1211

  日期：1993.4

  β-d-Ribofuranosides are stereoselectively synthesized in high yields directly from 2,3,5-tri-O-benzyl-d-ribofuranose and trimethylsilylated nucleophiles by the use of [catecholato(2−)-O,O′ ]oxotitanium and trifluoromethanesulfonic anhydride, while α-d-ribofuranosides are prepared predominantly in high yields in the coexistence of lithium perchlorate.

  通过使用[邻苯二酚（2-）-O、O′ ]氧钛和三氟甲磺酸酐，而 α-d-ribofuranosides 则主要是在高氯酸锂的作用下以高产率制备的。
• Stereoselective Syntheses of<i>α</i>-D- and<i>β</i>-D-Ribofuranosides Catalyzed by the Combined Use of Silver Salts and Their Partners
  作者：Naoyuki Shimomura、Teruaki Mukaiyama

  DOI：10.1246/bcsj.67.2532

  日期：1994.9

  α-d-Ribofuranosides are stereoselectively synthesized in high yields from 2,3,5-tri-O-benzyl-1-O-iodoacetyl-d-ribofuranose (1) and trimethylsilylated nucleophiles by the use of silver salts in the coexistence of 3 molar amounts of lithium perchlorate, while β-d-ribofuranosides are prepared predominantly in high yields by the reaction of 1 and trimethylsilylated nucleophiles or 2,3,5-tri-O-benzyl-d-ribofuranose and free alcohols by using [diphenyltin sulfide/silver salt] or [Lawesson’s reagent/silver salt] combined catalyst system.

  α-d-核呋喃糖苷是由 2,3,5-三-O-苄基-1-O-碘乙酰-d-核呋喃糖（1）和三甲基硅烷基化的亲核物通过使用银盐与 3 摩尔量的高氯酸锂共存进行立体选择性高产率合成的、而使用[二苯基硫化锡/银盐]或[Lawesson 试剂/银盐]组合催化剂体系，通过 1 和三甲基硅烷化亲核物或 2,3,5-三-O-苄基-d-呋喃三糖与游离醇的反应，主要可以高产率制备出 β-d-呋喃核苷。
• 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。
• Stereoselective Synthesis of 2-Amino-2-deoxy-β-D-glucopyranosides and Galactopyranosides by Using a Catalytic Amount of Tin(II) Trifluoromethanesulfonate
  作者：Teruaki Mukaiyama、Koki Matsubara

  DOI：10.1246/cl.1992.1755

  日期：1992.9

  In the presence of a catalytic amount of tin(II) trifluoromethanesulfonate, various 2-amino-2-deoxy-β-D-glucopyranosides or galactopyranosides are stereoselectively synthesized in good yields from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxy carbonylamino)-β-D-glucopyranose or galactopyranose and alkyl trimethylsilyl ethers, respectively.

  在催化量的三氟甲磺酸锡（II）存在下，可分别从 1,3,4,6-四-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苷和烷基三甲基硅醚立体选择性地合成各种 2-氨基-2-脱氧-β-D-吡喃葡萄糖苷或吡喃半乳糖苷，且产率良好。
• Stereoselective Synthesis of O-(2-Azido-2-deoxy-α-D-galactopyranosyl)-L-serine and -L-threonine Derivatives by Using the Catalytic Amount of Active Acidic Species
  作者：Koki Matsubara、Teruaki Mukaiyama

  DOI：10.1246/cl.1993.581

  日期：1993.3

  In the presence of a catalytic amount of SnCl3(ClO4) or SiCl3(ClO4), O-(2-azido-2-deoxy-α-D-galactopyranosyl)-L-serine and -L-threonine are stereoselectively synthesized in excellent yields from 1-O-acetyl-2-azido-2-deoxy-3,4,6-tri-O-benzyl-D-galactopyranose and trimethylsilylated L-serine or L-threonine, respectively.

  在催化量的 SnCl3(ClO4) 或 SiCl3(ClO4) 存在下，O-(2-叠氮基-2-脱氧-α-D-吡喃半乳糖基)-L-丝氨酸和-L-苏氨酸以优异的产率立体选择性合成分别来自1-O-乙酰基-2-叠氮基-2-脱氧-3,4,6-三-O-苄基-D-吡喃半乳糖和三甲基甲硅烷基化的L-丝氨酸或L-苏氨酸。