methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside | 69558-08-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside
• 英文别名: (2R,3R,4R,5R,6S)-2-methoxy-6-methyl-5-phenylmethoxy-3-prop-2-enoxyoxan-4-ol
• CAS: 69558-08-3
• 化学式: C₁₇H₂₄O₅
• 分子量: 308.375
• InChiKey: UQVXDSVBGLQIQC-BMQFZULRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside 在 palladium hydroxide - carbon selenium(IV) oxide 、 三氟化硼乙醚 、 氢气 、 sodium methylate 、 氰化汞 、 sodium hydride 、 溶剂黄146 、 mercury dibromide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 paraffin 为溶剂， 反应 82.0h， 生成 methyl 3-O-[3-O-methyl-2-O-(α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-2-O-(β-D-xylopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the unique terminal branched tetrasaccharide of Mycobacterium gordonae strain 990

  摘要：

  Mycobacterium gordonae strain 990 contains a unique oligosaccharide with branched sugar residue. A novel synthesis of the terminal tetrasaccharide-methyl 3-O-[3-O-methyl-2-O(alpha-L-rhamnopyranosyl)-alpha-L-rhamnopyranosyl]-2-O-(beta-D-xylopyranosyl)-alpha-L-rhamnopyranoside has been described. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00532-2
• 作为产物：
  描述：

  甲基 2,3-O-异亚丙基-alpha-L-吡喃鼠李糖苷 在 sodium hydroxide 、 四丁基溴化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.0h， 生成 methyl 2-O-allyl-4-O-benzyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  从克雷伯菌血清型40合成与多糖相关的二糖甲基糖苷及其在沉淀蛋白反应中的抑制作用的研究。

  摘要：

  alpha-D-Manp-（1 ---- 4）-alpha-L-Rhap（3），alpha-L-Rhap-（1 ---- 3）-beta-D-Galp（4 ），beta-L-Rhap-（1 ---- 3）-beta-D-Galp（5），beta-D-Galp-（1 ---- 2）-alpha-L-Rhap（6），合成了β-D-GlcpA-（1 ---- 2）-α-L-Rhap（7）并研究了它们在克雷伯菌血清型40免疫系统中的抑制反应。获得的结果仅与为K40抗原的重复单位提出的两个结构之一一致。

  DOI：

  10.1016/0008-6215(90)80085-h

文献信息

• Synthesis of the tetrasaccharide repeating-unit of the polysaccharide from Klebsiella type 23
  作者：Asim K. Ray、Nirmolendu Roy

  DOI：10.1016/0008-6215(90)84108-7

  日期：1990.2

  Methyl 2-O-allyl-4-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-beta-D- glucopyranosyl)-alpha-L-rhamnospyranoside was obtained by condensing methyl 2-O-allyl-4-O-benzyl-alpha-L-rhamnopyranoside with tetra-O-acetyl-alpha-D-glucopyranosyl bromide. Benzylation, removal of the allyl group, and condensation of the product with ethyl 6-O-acetyl-2,3,4-tri-O-benzyl-1-thio-beta-D-glucopyranoside gave methyl 2-O-(6-O-acetyl-2

  通过缩合甲基2，获得2-O-烯丙基-4-O-苄基-3-O-（2,3,4,6-四-O-乙酰基-β-D-吡喃吡喃糖基）-α-L-鼠李糖吡喃糖苷-O-烯丙基-4-O-苄基-α-L-鼠李吡喃糖苷与四-O-乙酰基-α-D-吡喃葡萄糖基溴化物。苯甲酰化，除去烯丙基，并将产物与乙基6-O-乙酰基-2,3,4-三-O-苄基-1-硫代-β-D-吡喃葡萄糖苷缩合，得到甲基2-O-（6 -O-乙酰基-2,3,4-三-O-苄基-α-D-吡喃葡萄糖基）-4-O-苄基-3-O-（2,3,4,6-四-O-苄基-β -D-吡喃葡萄糖基）-α-L-鼠李糖吡喃糖苷。O-脱乙酰基，产物与（2,3,4-三-O-乙酰基-α-D-吡喃葡萄糖基溴）甲基缩合，并除去保护基，得到3-O-β-D-吡喃葡萄糖基甲基-2-O- [6-O-（β-D-吡喃葡萄糖基糖醛酸）-α-D-吡喃葡萄糖基]-α-L-鼠李糖苷（13）。
• Acetolysis of 6-Deoxysugar Disaccharide Building Blocks:<i>exo</i>versus<i>endo</i>Activation
  作者：Luigi Cirillo、Emiliano Bedini、Michelangelo Parrilli

  DOI：10.1002/ejoc.200800696

  日期：2008.12

  Two different protocols for the mild and selective acetolysis of 6-deoxysugar methyl disaccharides under thermodynamic or kinetic control have been developed. The structures of the disaccharides obtained depend on the protocol used and, in the kinetically controlled cases, on the 6-deoxysugar configuration and protecting group pattern too. The behavior of 6-deoxyhexose oligosaccharides of different

  已经开发了两种不同的协议，用于在热力学或动力学控制下对 6-脱氧糖甲基二糖进行温和和选择性的乙酰化。获得的二糖的结构取决于所使用的方案，在动力学控制的情况下，也取决于 6-脱氧糖配置和保护基团模式。不同系列（鼠李糖、藜麦和岩藻糖）的 6-脱氧己糖寡糖在这两种反应条件下的行为已被研究并基于在乙酰化机制中外氧与内氧活化之间的竞争进行合理化。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
• A Versatile Strategy for the Synthesis of <i>N</i>-Acetyl-bacillosamine-Containing Disaccharide Building Blocks Related to Bacterial O-Antigens
  作者：Emiliano Bedini、Davide Esposito、Michelangelo Parrilli

  DOI：10.1055/s-2006-939057

  日期：——

  The synthetic path was then slightly modified to obtain a similar glycosyl donor with an axial acetyl group on position 4. This building block could be coupled to give a disaccharide, that after five steps (azido reduction, acetylation, O-deacetylation, mesylation, and azide substitution) afforded a bacillosamine-containing disaccharide with differently protected amino functions, in order to provide

  芽孢杆菌胺的 N-苯基三氟乙酰亚胺糖基供体，一种包含在来自病原菌的几种 0-抗原中的 2,4-二氨基糖，是从已知的全乙酰化 D-fucal 开始合成的，并被证明对与芽孢杆菌胺的高产偶联是有效的。含双糖。取决于溶剂和糖基受体，糖基化的立体选择性从中等到非常好。然后稍微修改合成路径以获得类似的糖基供体，在位置 4 上有一个轴向乙酰基。这个构建块可以偶联得到二糖，经过五个步骤（叠氮基还原、乙酰化、O-脱乙酰化、甲磺酰化和叠氮化物取代）提供了具有不同保护氨基功能的含杆胺二糖，
• First synthesis of an α-d-Fucp3NAc containing oligosaccharide: a study on d-Fucp3NAc glycosylation
  作者：Emiliano Bedini、Antonella Carabellese、Marialuisa Schiattarella、Michelangelo Parrilli

  DOI：10.1016/j.tet.2005.04.013

  日期：2005.6

  3-Acetainido-3.6-dideoxy-D-galactopyranose (D-Fucp3NAc) is an aminosugar almost exclusively found in phytopathogenic O-antigens. The glycosylation reaction involving D-Fucp3NAc donors was studied with several rhamnosyl acceptors, revealing, that the best yields and highest alpha-stereoselectivity were obtainable by coupling a N-phenyl trifluoroacetimidate glycosyl donor in a tertiary mixture (dioxane/DME/toluene 4:1:1) as solvent. For the first time a synthetic access to alpha-D-Fucp3NAc containing oligorhamnans, that are interesting molecules for studying the effects of O-antigen model oligosaccharides on the modulation of plant response to bacteria, was reported. An example is the pentasaccharide repeating unit of the major O-antigen component from Pseudomonas syringae pv. holci IMV 8300, which was synthesized as its methyl glycoside. (c) 2005 Elsevier Ltd. All rights reserved.
• The behaviour of deoxyhexose trihaloacetimidates in selected glycosylations
  作者：Daniela Comegna、Emiliano Bedini、Annalida Di Nola、Alfonso Iadonisi、Michelangelo Parrilli

  DOI：10.1016/j.carres.2007.02.009

  日期：2007.6

  Armed deoxyhexose glycosyl donors are very reactive and sometimes too uncontrollably activated in glycosylation reactions; yields can be thereby reduced, especially when unreactive glycosyl acceptors are involved. In this paper, the behaviour of a range of deoxyhexose trihaloacetimidate (trichloro- and N-phenyl trifluoro-) donors is compared in some selected glycosylations towards biologically relevant targets. The selected N-phenyl trifluoroacetimidates often afforded best results in terms of both donor synthesis and glycosylation yield. (c) 2007 Elsevier Ltd. All rights reserved.