2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate | 4196-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate
• 英文别名: alpha-D-Glucopyranose, 2,3,4,6-tetrakis-O-(phenylmethyl)-, 1-(4-nitrobenzoate)；[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl] 4-nitrobenzoate
• CAS: 4196-36-5
• 化学式: C₄₁H₃₉NO₉
• 分子量: 689.762
• InChiKey: IJTANGJQVDVKFH-ZWWYPIQLSA-N

物化性质

• 熔点：
  125.0-126.5 °C
• 沸点：
  793.7±60.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  51
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 (2R,3r,4s,5r,6r)-3,4,5-三s(苄氧基)-2-溴-6-(3-苯基丙基)四氢-2H-吡喃
  参考文献：
  名称：

  含有油酰基磷脂酰部分的磷脂酰-α-葡萄糖基甘油的合成。四异丙基二硅氧烷-1,3-二基（尖端）保护基在糖化学中的应用。第三部分1

  摘要：

  在这项研究中，我们证明了可以通过两步操作在α-葡萄糖基甘油二酸酯3的3'-和4'-羟基官能团处引入四异丙基二硅氧烷-1,3-二基保护基团以生成衍生物6。化合物6可以可以在其伯羟基官能团上与适当保护的磷脂酰部分9选择性缩合，得到保护的糖磷脂10a。磷脂酰部分9是通过将光学纯的1，2-二-O-油酰基-sn-甘油（8a）用磷酸二三唑酯7b磷酸化而获得的。最后，分别通过顺-4-硝基苯甲酰肟酸酯和氟离子从10a中除去2，4-二氯苯基和TIPS保护基，得到糖脂10c。

  DOI：

  10.1016/s0040-4020(01)82349-8
• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl 4-nitrobenzoate
  参考文献：
  名称：

  Combined Lewis acid and Brønsted acid-mediated reactivity of glycosyl trichloroacetimidate donors

  摘要：

  Biomimetic conditions for a synthetic glycosylation reaction, inspired by the highly conserved functionality of carbohydrate active enzymes, were explored. At the outset, we sought to generate proof of principle for this approach to developing catalytic systems for glycosylation. However, control reactions and subsequent kinetic studies showed that a stoichiometric, irreversible reaction of the catalyst and glycosyl donor was occurring, with a remarkable rate variance depending upon the structure of the carboxylic acid. It was subsequently found that a combination of Bronsted acid (carboxylic acid) and Lewis acid (MgBr2) was unique in catalyzing the desired glycosylation reaction. Thus, it was concluded that the two acids act synergistically to catalyze the desired transformation. The role of the catalytic components was tested with a number of control reactions and based on these studies a mechanism is proposed herein. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2013.09.011

文献信息

• Phosphotriester approach to the synthesis of α-glucosylated mono- and diphosphatidyl glycerols: bacterial cell-wall components
  作者：C.A.A. van Boeckel、J.J. Oltvoort、Jh. van Boom

  DOI：10.1016/s0040-4020(01)98907-0

  日期：1981.1

  phosphorylating agents, 2,2,2-tribromoethyl and 2-chlorophenyl phosphorodichloridate, were used with 1,2,4-triazole to assemble phosphotriester derivatives of protected α-glucosyl mono- and diphosphatidyl glycerols. Benzyl, allyl and pivaloyl groups were used for the protection of the hydroxyl functions of the glucose and glycerol moieties, respectively. The merits of the pivaloyl group are discussed. Finally

  两种双功能磷酸化剂2,2,2-三溴乙基和2-氯苯基二氯磷酸酯与1,2,4-三唑一起使用，以组装受保护的α-葡萄糖基单和二磷脂酰甘油的磷酸三酯衍生物。苄基，烯丙基和新戊酰基分别用于保护葡萄糖和甘油部分的羟基功能。讨论了新戊酰基的优点。最后，要特别注意将磷酸三酯转化为所需的磷酸二酯功能。
• Synthesis of Chiral Spiroacetals from Carbohydrates
  作者：Angeles Martín、José A. Salazar、Ernesto Suárez

  DOI：10.1021/jo960060g

  日期：1996.1.1

  Chiral spiroacetals of the 1,7-dioxaspiro[5.5]undecane, 1,6-dioxaspiro[4.5]decane, and 1,6-dioxaspiro[4.4]nonane types have been prepared from carbohydrates in pyranose or furanose forms. The spirocyclization reaction has been accomplished from a conveniently homologated carbohydrate by an intramolecular hydrogen abstraction reaction promoted by alkoxy radicals. Thus, 2,3,4,6-tetra-O-benzyl-1-deox

  由吡喃糖或呋喃糖形式的碳水化合物制备了1,7-二氧杂螺[5.5]十一烷，1,6-二氧杂螺[4.5]癸烷和1,6-二氧杂螺[4.4]壬烷类型的手性螺缩醛。螺环化反应已经通过由烷氧基自由基促进的分子内氢提取反应，从便利地同源的碳水化合物完成。因此，在（二乙酰氧基碘）苯存在下，用可见光光解2,3,4,6-四-O-苄基-1-脱氧-1-（3'-羟丙基）-α-D-吡喃葡萄糖（2）。和碘制得（1R）-（3）和（1S）-2,3,4,6-四-O-苄基-1-脱氧-D-吡喃葡萄糖-1-螺-2'-四氢呋喃的混合物（ 4）。甲基6-脱氧-6-（2'-羟乙基）-2,3,4-三-O-甲基-α-D-吡喃葡萄糖苷（8）的光解得到异构的螺缩醛甲基（5S）-（9）和（5R）-6-脱氧-5,2'-环氧-6-乙基-2,3，4-螺-O-甲基-α-D-吡喃葡萄糖苷（10）的螺中心现在位于C-5。[5.5]十一烷系列的螺缩醛：甲基（5R）-（19）和（5S）-6-脱氧-5
• Syntheses of 1-O-acylaldose derivatives via the corresponding O-glycosylpseudoureas
  作者：Hideo Tsutsumi、Yoshiharu Ishido

  DOI：10.1016/0008-6215(82)85008-8

  日期：1982.12

  Abstract A series of 1- O -acylaldose derivatives was prepared in good yield through the reaction of 1,3-dialkyl- O -glycosylpseudoureas with carboxylic acids.

  摘要通过1，3-二烷基-O-糖基假单胞菌与羧酸的反应，高收率地制备了一系列1-O-酰基醛糖衍生物。
• A Novel Glycosidation Promoted by the Combination of Trimethylsilyl Halide and Zinc Triflate.
  作者：Kunio HIGASHI、Hiroshi SUSAKI

  DOI：10.1248/cpb.40.2019

  日期：——

  A novel glycosidation method has been developed which utilizes a trimethylsilyl halide-zinc triflate catalyst system to activate various benzyl-protected fucosyl, glucosyl and galactosyl esters. The promoter system was extended to use benzyl-protected alkyl glycosides and N-2, 2, 2, -trichloroethoxycarbonyl-protected glucosaminyl and galactosaminyl acetates as glycosyl donors.

  我们开发了一种新型糖苷化方法，它利用三甲基硅卤化物-三late锌催化剂体系来激活各种苄基保护的岩藻糖基、葡萄糖基和半乳糖基酯。该促进剂体系已扩展到使用苄基保护的烷基糖苷和 N-2，2，2，-三氯乙氧羰基保护的葡萄糖氨酰和半乳糖氨酰醋酸盐作为糖基供体。
• Preparative synthesis of C-(α-d-glucopyranosyl)-alkenes and -alkadienes: Diels-alder reaction
  作者：Maria de Gracia Garcia Martin、Derek Horton

  DOI：10.1016/0008-6215(89)85066-9

  日期：1989.8

  The reaction of 2,3,4,6-tetra-O-benzyl-1-O-(p-nitrobenzoyl)-alpha-D-glucopyranose with (E)-penta-2,4-dienyltrimethylsilane and boron trifluoride etherate in acetonitrile afforded stereoselectively (E)-5-(tetra-O-benzyl-alpha-D-glucopyranosyl)-1,3-pentadiene in good yield. The readily available penta-O-benzoyl-alpha-D-glucopyranose reacted with allyltrimethylsilane in the presence of boron trifluoride

  2,3,4,6-四-O-苄基-1-O-（对硝基苯甲酰基）-α-D-吡喃葡萄糖与（E）-戊-2,4-二烯基三甲基硅烷和三氟化硼醚化物在乙腈中的反应以良好的收率得到立体选择性地（E）-5-（四-O-苄基-α-D-吡喃葡萄糖基）-1,3-戊二烯。在乙腈中，在三氟化硼醚化物的存在下，易于获得的五-O-苯甲酰基-α-D-吡喃葡萄糖与烯丙基三甲基硅烷反应，生成3-（四-O-苯甲酰基-α-D-吡喃葡萄糖基）-1-丙烯及其β异构体的产率分别为60％和2.3％。将马来酸酐的Diels-Alder环加成成二烯1可以高收率得到加成物顺式，顺式3-（四-O-苄基-α-D-吡喃葡萄糖基甲基）环己基-4-烯-1,2-二羧酸酐。