n-octyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

• 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-α-D-mannopyranoside
• 英文别名: octyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside；octyl-O-2,3,4,6-tetra-O-benzyl-α-D-mannopyranose；(2S,3S,4S,5R,6R)-2-octoxy-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• 化学式: C₄₂H₅₂O₆
• 分子量: 652.871
• InChiKey: LFJKORWCRRSQRS-LPAYBXTFSA-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

• 作为产物：
  描述：

  2-allylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 在 sodium methylate 、 silver trifluoromethanesulfonate 、 一氯化碘 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 14.0h， 生成 n-octyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  2-Allylphenyl glycosides as glycosyl donors for sugar coupling

  摘要：

  Glycosylations employing 2-allylphenyl glycoside, a new type of stable glycosyl donor, were optimized and explored with a variety of acceptors promoted by ICl/AgOTf. The utility of the protocol was further demonstrated with an efficient synthesis of the disaccharide fragment of bleomycins. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.01.022

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。
• 2-Allyloxyphenyl glycoside as a new and stable type of glycosyl donors
  作者：Jinq-Chyi Lee、Guan-Rong Pan、Suvarn S. Kulkarni、Shun-Yuan Luo、Chun-Chen Liao、Shang-Cheng Hung

  DOI：10.1016/j.tetlet.2005.12.127

  日期：2006.3

  A high-yielding coupling of a new and stable type of glycosyl donors, namely 2-allyloxyphenyl glycoside, with a variety of alcohols via NIS/TfOH reagent combination as effective activators at room temperature is described here. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• Novel stereocontrolled α- and β-glycosidations of mannopyranosyl sulfoxides using environmentally benign heterogeneous solid acids
  作者：Hideyuki Nagai、Kanako Kawahara、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/s0040-4039(01)00674-8

  日期：2001.6

  The environmentally benign and stereocontrolled glycosidations of mannopyranosyl sulfoxides and alcohols using a heterogeneous solid acid, Nafion-H or sulfated zirconia (SO4/ZrO2) as a new activator for the direct syntheses of both the alpha- and beta -mannopyranosides have been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• A novel promoter, heteropoly acid, mediated chemo- and stereoselective sulfoxide glycosidation reactions
  作者：Hideyuki Nagai、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/s0040-4039(00)01821-9

  日期：2000.12

  The chemo- and stereoselective glycosidations of sulfinylglycosides and alcohols using a heteropoly acid, H3PW12O40, as a new promoter have been developed. (C) 2000 Elsevier Science Ltd. All rights reserved.