methyl 4,6-O-benzylidene-2,3-di-O-allyl-α-D-glucopyranoside | 13035-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 4,6-O-benzylidene-2,3-di-O-allyl-α-D-glucopyranoside
• 英文别名: (4aR,6S,7R,8S,8aR)-6-methoxy-2-phenyl-7,8-bis(prop-2-enoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 13035-23-9
• 化学式: C₂₀H₂₆O₆
• 分子量: 362.423
• InChiKey: FMKYMGOFTWEBLP-LOZDCHMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  methyl 4,6-O-benzylidene-2,3-di-O-allyl-α-D-glucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 methyl 2,3-di-O-allyl-4,6-di-O-p-bromobenzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis, crystalline structure, conformational analysis, and azidolysis of methyl 2,3-anhydro-α-d-manno- and -allo-pyranoside p-bromobenzyl

  摘要：

  Methyl 2,3-anhydro-4,6-di-O-p-bromobenzyl-alpha-D-allopyranoside (6) was synthesized from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside (1) via the intermediate methyl 4,6-di-O-p-bromobenzyl-2,3-di-O-p-tolylsulfonyl-alpha-D-glucopyranoside. Treatment of 6 with sodium azide selectively afforded methyl 3-azido-4,6-di-O-p-bromobenzyl-3-deoxy-alpha-D-glucopyranoside in 70% yield. Methyl 2,3-anhydro-4,6-di-O-p-bromobenzyl-(17) and methyl 2,3-anhydro-4,6-di-O-benzyl-alpha-D-mannopyranoside (18) were obtained from 1 via the intermediates methyl 4,6-di-O-p-bromobenzyl- and methyl 4,6-di-O-benzyl-2-O-p-tolylsulfonyl-alpha-D-glucopyranoside. Azidolysis of 17 and 18 with sodium azide in the presence of tetraethylammonium chloride in N,N-dimethylformamide gave the respective 3-azidoaltropyransides, in yields of 80%, by exclusive 3-attack. The crystal structure of compound 6 is orthorhombic with a space group of P2(1)2(1)2(1), and the 2,3-anhydropyranose moiety is in an almost ideal degrees-H-5 half-chair conformation. The crystals of 17 are also orthorhombic, belonging to space group P2(1)2(1)2(1), but the conformation is a hybrid of the degrees-H-5 half-chair and the degrees-E sofa. Analysis by NMR spectroscopy suggests that in solution in CDCl3 the conformation of 17 remains the same as, and that of 6 undergoes a change from, the respective solid-state conformations.

  DOI：

  10.1016/0008-6215(92)80086-g
• 作为产物：
  描述：

  甲基-4,6-O-亚苄基-Α-D-吡喃葡糖苷 在 4 A molecular sieve 、 四丁基溴化铵 、 sodium hydride 、 二正丁基氧化锡 作用下， 反应 31.33h， 生成 methyl 4,6-O-benzylidene-2,3-di-O-allyl-α-D-glucopyranoside
  参考文献：
  名称：

  Corrie, John E. T., Journal of the Chemical Society. Perkin transactions I, 1993, # 18, p. 2161 - 2166

  摘要：

  DOI：

文献信息

• <i>p</i>-Siletanylbenzylidene Acetal:  Oxidizable Protecting Group for Diols
  作者：Sarah E. House、Kevin W. C. Poon、Hubert Lam、Gregory B. Dudley

  DOI：10.1021/jo052015r

  日期：2006.1.1

  Hydrogen peroxide oxidation of benzylidene acetals (and derivative benzyl ethers) that incorporate a siletane ring at the para position creates a deprotection pathway without affecting other important chemical properties of the benzylidene acetal, such as regioselective reductive ring opening.

  在对位并入甲硅烷基环的亚苄基乙缩醛（和衍生物苄基醚）的过氧化氢氧化可形成脱保护途径，而不会影响亚苄基乙缩醛的其他重要化学性质，例如区域选择性还原性开环。
• Synthesis of substituted titanocene dichloride derivatives by hydrosilylation
  作者：Tomáš Strašák、Jindřich Karban、Lucie Červenková Št'astná、Lucie Maixnerová、Anna Březinová、Martin Bernard、Radek Fajgar

  DOI：10.1016/j.jorganchem.2014.06.009

  日期：2014.10

  Substituted titanocene complexes have been prepared by hydrosilylation of organic substrates containing a terminal double bond by cyclopentadienyl complexes of titanium bearing a Si–H functional group. This new synthetic protocol is demonstrated by synthesis of mono-, bi- and trihomonuclear complexes. The structures of prepared compounds have been characterized by standard methods (NMR, IR, and HRMS).

  取代的钛茂配合物是通过将带有末端双键的有机底物通过带有Si-H官能团的钛的环戊二烯基配合物氢化硅烷化而制备的。单，双和三核复合物的合成证明了这种新的合成方案。制备的化合物的结构已通过标准方法（NMR，IR和HRMS）进行了表征。
• Chirale Kronenether mit integriertem 1,4-verbrückten d-Glucopyranose-Baustein
  作者：Ralf Miethchen、Volker Fehring

  DOI：10.1055/s-1998-4480

  日期：1998.1

  Carbohydrate-Based Crown Ethers Containing 1,4-Linked d-Glucopyranose Moieties

  含 1,4-连接的 d-吡喃葡萄糖分子的碳水化合物冠醚
• Removal of<i>O</i>-Benzyl Protective Groups by Catalytic Transfer Hydrogenation
  作者：Tadeusz Bieg、Wiesław Szeja

  DOI：10.1055/s-1985-31113

  日期：——
• BIEG, TADEUSZ;SZEJA, WIESLAW
  作者：BIEG, TADEUSZ、SZEJA, WIESLAW

  DOI：——

  日期：——