benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopiranoside | 86833-19-4

• 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: benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopiranoside
• 英文别名: benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside；(2R,4aR,6S,7R,8R,8aR)-2-phenyl-6,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 86833-19-4
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: FCENHFYMICMPTH-XXVOEFFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopiranoside 在 四氧化锇 、 N-甲基吲哚酮 、 硼烷四氢呋喃络合物 、 草酰氯 、 三氟甲磺酸二丁硼 、 TEA 、 四丁基溴化铵 、 sodium hexamethyldisilazane 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w
• 作为产物：
  描述：

  benzyl 4,6-O-benzylidene-2-O-(p-toluenesulfonyl)-α-D-glucopyranoside 在 barium dihydroxide 、 sodium tetrahydroborate 、 barium(II) oxide 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 benzyl 3-O-benzyl-4,6-O-benzylidene-α-D-glucopiranoside
  参考文献：
  名称：

  Total Synthesis of Desferrisalmycin B

  摘要：

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.

  DOI：

  10.1021/ja028386w

文献信息

• Highly functionalized, enantiomerically pure furo[x,y-c]pyrans via alkylidenecarbenes derived from sugar templates: synthesis and mechanism study via computational chemistry
  作者：Albert Nguyen Van Nhien、Romaric Cordonnier、Marie-Delphine Le Bas、Sébastien Delacroix、Elena Soriano、José Marco-Contelles、Denis Postel

  DOI：10.1016/j.tet.2009.08.080

  日期：2009.11

  method for the generation of alkylidenecarbenes based on the reaction of trimethylsilylazide/Bu2SnO with α-cyanomesylates has been applied to readily available sugar derivatives for the synthesis of highly functionalized, enantiomerically pure furo[x,y-c]pyrans. The furo[x,y-c]pyran heterocyclic ring system is present in a number of natural or non-natural products of biological interest such as the miharamycins

  基于三甲基甲硅烷基叠氮化物/ Bu 2 SnO与α-氰基甲磺酸酯反应生成亚烷基卡宾的新方法已应用于容易获得的糖衍生物，用于合成高度官能化，对映体纯的呋喃[ x，y - c ]吡喃。呋喃[ x，y - c ]吡喃杂环系统存在于许多具有生物学意义的天然或非天然产物中，例如米拉霉素，应引起特别注意。本新方法的范围和程度已通过对起始糖前体（d-葡萄糖，d半乳糖等），在HEXO-α（β） - d -pyranoside形式，轴承也不同ø -保护基，该取代基的绝对构型的在异头位置的影响，位置（C-2， - 3和-4）在吡喃核上的亚烷基碳烯种类，以及在1,5 C–H键插入过程中“碳供体”处的取代（H或Ph）。总体而言，使用这些关键的1,5个C–H键插入反应，可合成呋喃[ x，y - c吡喃，很难用其他方法从中等到良好的产率制备。为了检查亚烷基卡宾的反应性，我们使用密度泛函理论对各种亚烷基卡宾衍生物插入C–H键的插入反应进行了系统的研究。
• Hydrogenolysis of the isomeric 1,2:4,6-di-O-benzylidene-α-d-glucopyranose derivatives with the LiAlH4AlCl3 reagent
  作者：András Lipták、János Imre、János Harangi、Pál Nánási

  DOI：10.1016/0008-6215(83)88111-7

  日期：1983.6

  Abstract Both isomers of 1,2:4,6-di- O -benzylidene-α- d -glucopyranose (and their 3- O -acetyl and 3- O -benzyl derivatives) have been prepared and their 1 H- and 13 C-n.m.r. spectra assigned. The mode of hydrogenolysis of the dioxolane ring in these isomers by the LiAlH 4 AlCl 3 reagent is determined by the configuration at the acetal carbon and is independent of the electronic character of the

  摘要制备了1,2：4,6-二-O-亚苄基-α-d-吡喃葡萄糖的两个异构体（及其3-O-乙酰基和3-O-苄基衍生物），并确定了它们的1 H-和13 Cn .mr光谱已分配。LiAlH 4 ＝ AlCl 3试剂在这些异构体中二氧戊环的氢解方式由乙缩醛碳上的构型决定，并且与两个氧原子的电子特性无关。
• Synthesis of a peracetylated stereoisomer of De Rosa's calditol: Some questions about the correctness of the original structure assigned to this natural product
  作者：Antony J. Fairbanks、Pierre Sinaỹ

  DOI：10.1016/0040-4039(94)02388-r

  日期：1995.2

  Comparison of the C-13 nmr spectrum of the nonacetate of a synthetic stereoisomer of calditol with that of the nonacetate of the natural product, combined with a comparison of the C-13 nmr spectrum of the peracetate of a hexitol derived from calditol with all known peracetates of open chain hexitols, invalidates the originally proposed structure.
• Total Synthesis of Desferrisalmycin B
  作者：Li Dong、John M. Roosenberg、Marvin J. Miller

  DOI：10.1021/ja028386w

  日期：2002.12.1

  The first total synthesis of a naturally occurring siderophore antibiotic, desferrisalmycin B, is described, and the configuration of the unknown stereocenter is assigned. The synthesis features a synthetic strategy of constructing the novel amino-heptopyranoside component by stereoselective dihydroxylation followed by a Bose-modified Mitsunobu reaction. Through this convergent approach, other members of salmycins should also be synthetically accessible.