Cyclohexylmethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 133339-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Cyclohexylmethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: cyclohexhyl 3,4,6-ti-O-acetyl-2-(2,2,2-trichloroethoxycarbonylamino)-2-deoxy-α-D-glucopyranoside；[(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(cyclohexylmethoxy)-5-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 133339-64-7
• 化学式: C₂₂H₃₂Cl₃NO₁₀
• 分子量: 576.856
• InChiKey: AKOAHPBKDXKIIT-WAPOTWQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  Cyclohexylmethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 三甲基溴硅烷 、 zinc dibromide C₆H₁₁CH₂OH 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到Cyclohexylmethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  A novel glycoside anomerization catalyzed by trimethylsilyl bromide and zinc bromide in combination.

  摘要：

  当三甲基溴硅烷（TMSBr）和溴化锌组合用作催化剂时，发生了一种新型的糖苷异构化反应。在醇存在下，用 TMSBr 和溴化锌处理 β-糖苷，可得到良好产率的异构化产物。

  DOI：

  10.1248/cpb.39.590

文献信息

• Direct Transformation of O-Glycosides into Other O-Glycosides Using Trimethylsilyl Bromide and Zinc Bromide.
  作者：Kunio HIGASHI、Kiyoshi NAKAYAMA、Emiko SHIOYA、Tsuneo KUSAMA

  DOI：10.1248/cpb.40.1042

  日期：——

  We have succeeded in developing a novel glycosidation catalyzed by a combination of trimethylsilyl bromide (TMSBr) and a Lewis acid using simple O-glycosides as glycosyl donors. Treatment of benzyl 2-deozy-2-tri-chloroethoxycarbonylamino-D-glucopyranoside with TMSBr and zinc bromide in the presence of glycosyl acceptors gave α-O-glycosides in moderate to high yields. Zinc triflate and tin(II)triflate were also found to be effective as the Lewis acid. This new methodology is applicable to methyl D-glucopyranoside.

  我们成功开发了一种新型的糖苷化反应，该反应是由三甲基氯化铵（TMSBr）和路易斯酸的组合催化，使用简单的O-糖苷作为糖苷供体。将苄基2-脱氧-2-三氯乙氧羧酰胺-D-葡萄糖吡喃糖苷与TMSBr和溴化锌在糖苷受体存在下处理，获得了中到高产率的α-O-糖苷。此外，三氟甲苯酸锌和亚锡三氟甲苯酸也被发现作为路易斯酸有效。该新方法适用于甲基D-葡萄糖吡喃糖苷。
• 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。
• Novel stereoselective glycosidation by the combined use of trityl halide and Lewis acid.
  作者：Kunio HIGASHI、Kiyoshi NAKAYAMA、Tsunehiko SOGA、Emiko SHIOYA、Kouichi UOTO、Tsuneo KUSAMA

  DOI：10.1248/cpb.38.3280

  日期：——

  A Novel stereoselective glycosidation was achieved by the combined use of trityl halide and Lewis acid under mild reaction conditions. The stereoselectivity was found to be drastically changed by the presence of trityl halide.

  在温和的反应条件下，联合使用三苯甲基卤化物和路易斯酸实现了一种新型的立体选择性糖苷化反应。研究发现，三苯甲基卤化物的存在会极大地改变立体选择性。
• Matsubara, K.; Mukaiyama, T., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2365 - 2382
  作者：Matsubara, K.、Mukaiyama, T.

  DOI：——

  日期：——
• HIGASHI, KUNIO;NAKAYAMA, KIYOSHI;SOGA, TSUNEHIKO;SHIOYA, EMIKO;UOTO, KOUI+, CHEM. AND PHARM. BULL., 38,(1990) N2, C. 3280-3282
  作者：HIGASHI, KUNIO、NAKAYAMA, KIYOSHI、SOGA, TSUNEHIKO、SHIOYA, EMIKO、UOTO, KOUI+

  DOI：——

  日期：——