n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside | 267890-72-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside
• 英文别名: octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside；octyl-O-2,3,4,6-tetra-O-benzyl-β-D-mannopyranose；(2R,3S,4S,5R,6R)-2-octoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 267890-72-2
• 化学式: C₄₂H₅₂O₆
• 分子量: 652.871
• InChiKey: LFJKORWCRRSQRS-LLGAQKOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 在 palladium dihydroxide 环己烯 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 正辛基 beta-D-吡喃甘露糖苷
  参考文献：
  名称：

  A simple polar deacetylated caloporoside derivative is a positive modulator of the GABAA chloride channel complex in cortical mammalian neurones

  摘要：

  Synthesis of octyl-O-beta-D-mannopyranoside, a caloporoside analogue was achieved by the activation of 2,3,4,6-tetra-O-benzyl-1-O-1',3'2'-dioxaphosphacyclohexane-alpha,beta-D-mannopyranosyl-2-oxide with TMSOTf (Trimethyl silyl triflate) and subsequent debenzylation. At 100 mu M the molecule significantly and reversibly increased the magnitude of GABA(A) currents evoked in cultured rat pyramidal neurones whilst concomitantly reducing the incidence of spontaneous synaptic activity. These results contradict earlier proposals that such molecules bind to the TBPS (tert-Butylbicyclophosphorothionate) site to block the chloride channel. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00330-9
• 作为产物：
  描述：

  辛醇 、 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl fluoride 在 硫酸酯 、 zirconium(IV) oxide 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 、 n-octyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Novel Stereocontrolled Glycosidations Using a Solid Acid, SO₄/ZrO₂, for Direct Syntheses of α- and β-Mannopyranosides

  摘要：

  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。

  DOI：

  10.1055/s-1998-1741

文献信息

• 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。
• A new glycosylation strategy for the synthesis of mannopyranosides
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(99)00487-5

  日期：2000.1

  Activation of the anomeric centre of 1-O-2,3,4,6-tetra-O-benzyl-D-mannopyranos propane-1,3-diyl phosphate in the presence of trimethylsilyl triflate allowed the preparation of alpha- or beta-manno-linked glycosides. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Formation of O-Glycosidic Linkages from 1-Hydroxy Sugars by Bismuth(III) Triflate-Catalyzed Dehydrative Glycosidation
  作者：Takashi Yamanoi、Ryo Inoue、Sho Matsuda、Kazuya Iwao、Yoshiki Oda、Akihiro Yoshida、Keita Hamasaki

  DOI：10.3987/com-08-s(f)41

  日期：——

  This paper describes the direct formation of various O-glycosidic linkages from 1-hydroxy sugars by bismuth(III) triflate-catalyzed dehydrative glycosidation. The condensation reactions of 1-hydroxy sugars with some primary alcohols in the presence of only 5 mol% bismuth(III) triflate at reflux temperature for 15 min in dichloromethane afforded O-glycosides in good yields. An 1,6-anhydro-beta-D-glucopyranosidic linkage was formed by the intramolecular condensation of the corresponding 1-hydroxy sugar performed with similar reaction conditions using 5 mol% bismuth(III) triflate. A reaction using 10 mol% bismuth(III) triflate at room temperature in dichloromethane promoted the self- or cross-condensations of I-hydroxy sugars to produce several kinds of 1,1'-disaccharides. This paper reports some important properties of bismuth(III) triflate catalyzed dehydrative glycosidation using 1-hydroxy sugars to form various O-glycosidic linkages.
• A simple polar deacetylated caloporoside derivative is a positive modulator of the GABAA chloride channel complex in cortical mammalian neurones
  作者：George Lees、Paul L Chazot、Hariprasad Vankayalapati、Gurdial Singh

  DOI：10.1016/s0960-894x(00)00330-9

  日期：2000.8

  Synthesis of octyl-O-beta-D-mannopyranoside, a caloporoside analogue was achieved by the activation of 2,3,4,6-tetra-O-benzyl-1-O-1',3'2'-dioxaphosphacyclohexane-alpha,beta-D-mannopyranosyl-2-oxide with TMSOTf (Trimethyl silyl triflate) and subsequent debenzylation. At 100 mu M the molecule significantly and reversibly increased the magnitude of GABA(A) currents evoked in cultured rat pyramidal neurones whilst concomitantly reducing the incidence of spontaneous synaptic activity. These results contradict earlier proposals that such molecules bind to the TBPS (tert-Butylbicyclophosphorothionate) site to block the chloride channel. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides
  作者：Kazunobu Toshima、Hideyuki Nagai、Ken-ichi Kasumi、Kanako Kawahara、Shuichi Matsumura

  DOI：10.1016/j.tet.2004.04.071

  日期：2004.6

  Novel alpha- and beta-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl alpha-fluorides with several alcohols using SO4/ZrO2 in MeCN proceeded alpha-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with beta-stereo selectivity. Thus, both the alpha- and beta-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations. (C) 2004 Elsevier Ltd. All rights reserved.