cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside | 128820-60-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclohexylmethyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside
• 英文别名: (2R,3S,4S,5R,6R)-2-(cyclohexylmethoxy)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 128820-60-0
• 化学式: C₄₁H₄₈O₆
• 分子量: 636.829
• InChiKey: CEVWXHFLEZHMLS-NEJZJLHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 、 环己甲醇 在 3,11-dimethoxydinaphtho[2,1-b:1',2'-d]thiophene 作用下， 以 甲苯 为溶剂， 以4%的产率得到
  参考文献：
  名称：

  Photoinduced Glycosylation Using a Diarylthiophene as an Organo Lewis Photoacid Catalyst

  摘要：

  摘要报告了以 3,11-二甲氧基二萘并噻吩为有机路易斯光酸催化剂，在长波紫外-LED 光（385 nm）照射下，对三氯乙酰亚氨酸供体和几种醇进行光诱导糖基化的研究。反应在温和的反应条件下顺利进行，以良好至高产率得到相应的糖苷。此外，本糖基化方法适用于多种三氯乙酰亚氨酸供体和受体。此外，二萘硫茚催化剂可回收和重复使用，而不会降低效率。此外，这种糖基化方法还成功地应用于生物活性天然产物胆甾烯基 6-O-肉豆蔻酰-α-葡萄糖苷的全合成。

  DOI：

  10.1002/ejoc.202300287

文献信息

• Novel Dehydrative Glycosidations of 1-Hydroxy Sugars Using a Heteropoly Acid
  作者：Kazunobu Toshima、Hideyuki Nagai、Shuichi Matsumura

  DOI：10.1055/s-1999-2869

  日期：1999.9

  Novel and convenient dehydrative glycosidations of 1-hydroxy glycosyl donors have been developed. Several O-benzylated 1-hydroxy sugars are effectively cross-coupled with a variety of alcohols to give the corresponding O-glycosides in high yields with good α-stereoselectivities by using the heteropoly acid, H4SiW12O40.

  我们开发出了新颖便捷的 1-羟基糖基给体脱水糖苷化反应。通过使用杂多酸 H4SiW12O40，几种 O-苄基化的 1-羟基糖与多种醇有效地交叉偶联，得到相应的 O-糖苷，产量高，δ-立体选择性好。
• Photo-induced glycosylation using reusable organophotoacids
  作者：Ryosuke Iwata、Kanjiro Uda、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1039/c4cc04753b

  日期：——

  The glycosylation reactions of glycosyl trichloroacetimidates and several alcohols using an organophotoacid as an activator under photoirradiation proceeded smoothly to give the corresponding glycosides in high yields.

  糖基三氯乙酰亚胺和几种醇的糖基化反应，在光照条件下使用有机光酸作为活化剂进行，顺利进行，产率较高地得到相应的糖苷。
• Novel .ALPHA.-Mannoside Synthesis Promoted by the Combination of Trimethylsilyl Chloride and Zinc Triflate.
  作者：Hiroshi SUSAKI、Kunio HIGASHI

  DOI：10.1248/cpb.41.201

  日期：——

  α-Mannosides were obtained in good yields and with good selectivity directly form benzyl-protected mannopyranosyl p-nitrobenzoate or acetate using a trimethylsilyl chloride-zinc triflate catalyst system.

  使用三甲基氯硅烷-三氟甲磺酸锌催化剂体系，直接形成苄基保护的吡喃甘露糖基对硝基苯甲酸酯或乙酸酯，以良好的产率和良好的选择性获得α-甘露糖苷。
• Novel Stereocontrolled Glycosidations Using a Solid Acid, SO₄/ZrO₂, for Direct Syntheses of <i>α</i>- and <i>β</i>-Mannopyranosides
  作者：Kazunobu Toshima、Ken-ichi Kasumi、Shuichi Matsumura

  DOI：10.1055/s-1998-1741

  日期：1998.6

  Novel stereocontrolled glycosidations using an environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), for direct syntheses of α- and β-mannopyranosides have been developed. The glycosidations of the totally benzylated mannopyranosyl fluoride 1 and various alcohols using SO4/ZrO2 in CH3CN at 40 °C for 15 h exclusively gave the corresponding α-mannopyranosides. On the other hand, the corresponding β-mannopyranosides were selectively obtained by the glycosidations of 1 and various alcohols employing SO4/ZrO2 in the presence of molecular sieves 5 Å in Et2O at 25 °C for 15 h.

  使用环保固体酸硫酸化氧化锆 (SO4/ZrO2) 的新型立体控制糖苷化，用于直接合成 α- 和 β- 吡喃甘露糖苷，已经开发出来。完全苄基化的吡喃甘露糖基氟化物 1 和各种醇在 CH3CN 中于 40 °C 下使用 SO4/ZrO2 进行糖苷化 15 小时，专门得到相应的 α-吡喃甘露糖苷。另一方面，相应的β-吡喃甘露糖苷是通过1 和各种醇的糖苷化选择性获得的，使用SO4/ZrO2 在分子筛5 Å 的Et2O 存在下在25 °C 15 小时。
• Stereocontrolled Photoinduced Glycosylation Using an Aryl Thiourea as an Organo photoacid
  作者：Tomoya Kimura、Takahiro Eto、Daisuke Takahashi、Kazunobu Toshima

  DOI：10.1021/acs.orglett.6b01404

  日期：2016.7.1

  Photoinduced glycosylation of alcohols with alpha-glucosyl trichloroacetimidates, using aryl urea and thioureas as organo photoacids, was examined under long wavelength UV (ultraviolet) irradiation. The results show, for the first time, that such glycosylations proceed effectively to give the corresponding glycosides in high yields. In addition, high beta-stereoselectivity was obtained under high concentration conditions, whereas high alpha-stereoselectivity was realized under low concentration conditions.