3-O-benzyl-4,6-O-benzylidene-D-glucal | 110522-37-7

• 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: 3-O-benzyl-4,6-O-benzylidene-D-glucal
• 英文别名: 4,6-O-benzylidene-3-O-benzyl-D-glucal；(4aR,8R,8aS)-2-phenyl-8-phenylmethoxy-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• CAS: 110522-37-7
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: PJWQVCOHIKOJPW-WRURNZQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-4,6-O-benzylidene-D-glucal 在 叠氮化锂 、 二甲基二环氧乙烷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 2.0h， 生成 (4aR,6R,7R,8R,8aR)-6-Azido-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol
  参考文献：
  名称：

  Synthesis of D-glycopyranosyl azides from 1,2-anhydrosugars using lithium azidohydridodiisobutylaluminate

  摘要：

  1,2-Anhydrosugars were transformed regio- and stereoselectively into the corresponding D-glycopyranosyl azides in high yield by treatment with lithium azidohydridodiisobutylaluminate in THE (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02435-6
• 作为产物：
  描述：

  phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside 生成 3-O-benzyl-4,6-O-benzylidene-D-glucal
  参考文献：
  名称：

  FERNANDEZ-MAYORALAS, ALFONSO;MARRA, ALBERTO;TRUMTEL, MICHEL;VEYRIERES, AL+, TETRAHEDRON LETT., 30,(1989) N9, C. 2537-2540

  摘要：

  DOI：

文献信息

• Nitro-polyols via Pyridine Promoted C═C Cleavage of 2-Nitroglycals. Application to the Synthesis of (−)-Hyacinthacine A1
  作者：Shengbiao Tang、De-Cai Xiong、Shende Jiang、Xin-Shan Ye

  DOI：10.1021/acs.orglett.5b03607

  日期：2016.2.5

  A mild and convenient transformation for the synthesis of nitro-polyols is described. The nitro-polyol derivatives were prepared either from 2-nitroglycals via a pyridine-promoted scission of the carbon–carbon double bond or from glycals via a sequential nitration–scission procedure. The generated nitro-polyols could undergo a stereoselective Michael addition reaction. The utility of the addition products

  描述了用于合成硝基多元醇的温和且方便的转化。硝基多元醇衍生物是由2-硝基糖类通过吡啶促进的碳-碳双键断裂或序贯硝化-断裂过程由糖类制备的。生成的硝基多元醇可能会发生立体选择性迈克尔加成反应。通过（-）-扁豆碱A1和7a- epi -（-）-扁豆碱A1的简明合成来举例说明添加产物的效用。
• Selective formation of C-2 azidodeoxy-d-glucose derivatives from d-glucal precursors using the azidonitration reaction
  作者：Peter H. Seeberger、Susanne Roehrig、Peter Schell、Yuan Wang、William J. Christ

  DOI：10.1016/s0008-6215(00)00111-7

  日期：2000.8

  groups, were subjected to the azidonitration reaction to furnish the corresponding C-2 azidodeoxy-D-glucoses. 4,6-O-Isopropylidene-3-O-triisopropylsilyl-D-arabino-hex-1-enit ol afforded 2-azido-2-deoxy-4,6-O-isopropylidene-3-O-triisopropylsilyl-D-gluco pyranosyl nitrate and its D-manno isomer in a 20:1 ratio. These findings allow the azidonitration reaction to be now used for the preparation of a variety

  一系列由环缩醛保护基保护以构象地约束C-4和C-6羟基的葡聚糖进行叠氮化反应，以提供相应的C-2叠氮基-D-葡萄糖。4,6-O-异亚丙基-3-O-三异丙基甲硅烷基-D-阿拉伯-十六烷基-1-烯醇得到2-叠氮基-2-脱氧-4,6-O-异亚丙基-3-O-三异丙基甲硅烷基-D-葡萄糖硝酸吡喃酯及其D-甘露糖异构体的比例为20：1。这些发现使得叠氮基化反应现在可用于由受保护的葡糖前体制备各种葡糖胺结构单元。
• A Novel Aspect in Chlorination of D-Glucal Derivatives. Important Roles of the 4,6-<i>O</i>-Benzylidene Group and Substituent at<i>C</i>-3 in the Selective Formation of β-D-<i>Manno</i>and β-D-<i>Arabino</i>Isomers
  作者：Tohru Sakakibara、Takumi Yatabe、Kohji Yoshino、Yoshiharu Ishido

  DOI：10.1246/cl.1987.7

  日期：1987.1.5

  In contrast with the precedent reports described in peracetyl-and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4,6-O-benzylidene-D-glucal in carbon tetrachloride predominantly occurred from the β-side to give the β-D-manno and β-D-arabino adducts, respectively.

  与过乙酰基-和过苄基-D-glucal 中描述的先例报告相反，四氯化碳中 3-O-乙酰基-和 3-deoxy-4,6-O-benzylidene-D-glucal 的氯化主要发生在 β-侧分别给出β-D-甘露糖和β-D-阿拉伯加合物。
• Stereoselective Synthesis of 2-Deoxy-β-glycosides From Glycal Precursors. 1. Stereochemistry of the Reactions of ?-Glucal Derivatives with Phenylsulfenyl Chloride and Phenylselenenyl Chloride
  作者：W Roush*

  DOI：10.1016/s0040-4020(97)00571-1

  日期：1997.6.30
• Aureolic acid antibiotics: a simple method for 2-deoxy-.beta.-glycosidation
  作者：Subban Ramesh、Neelu Kaila、Gurmit Grewal、Richard W. Franck

  DOI：10.1021/jo00288a003

  日期：1990.1