allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside | 136737-75-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3R,4R,5R,6R)-5-benzoyloxy-4-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 136737-75-2
• 化学式: C₂₃H₂₄O₇
• 分子量: 412.439
• InChiKey: SMUZDUIELUJCKR-QCUMIWAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 三氟化硼乙醚 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 palladium dichloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 Ethyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzoyl-1-thio-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of a group of diosgenyl saponins with combined use of glycosyl trichloroacetimidate and thioglycoside donors

  摘要：

  通过结合使用糖基三氯乙亚胺酯和硫代糖苷，一系列天然薯蓣皂苷元的皂苷（1-6）被高效地合成，无论是逐步合成还是“一锅法”合成。三氯乙亚胺酯作为糖基化反应中糖基三氯乙亚胺酯的临时羟基保护组，表现出高效性。硫代糖苷参与的糖基化反应中，分子的烷硫基转移被证实是一种常见的副反应。

  DOI：

  10.1039/a909218h
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 溶剂黄146 、 乙酰氯 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 allyl 2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  合成由α-（1→2）-和α-（1→3）连接的鼠李糖聚糖主链和GlcNAc侧链组成的寡糖的一般方法

  摘要：

  已经开发了用于合成由具有GlcNAc侧链的（1→2）-和（1→3）-连接的鼠李糖寡糖组成的寡糖的一般方法。例如，在植物致病性细菌丁香假单胞菌pv的脂多糖的O多糖部分中的两个十糖的高效且收敛的合成。获得了ribicola NCPPB 1010。这两个十糖分别由O多糖重复单元I + II和II + I组成。烯丙基3- ø -乙酰基-4- ö苯甲酰基α-L-吡喃鼠李糖苷，烯丙基2- ø -苯甲酰基-3- ø -氯乙酰-α-L-吡喃鼠李糖苷，2,4-二- ö苯甲酰基-3- ø -氯乙酰-α-L-吡喃鼠李糖三氯乙酰亚胺酯，和3- ö -乙酰基-2,4-二- ö苯甲酰基α-L-吡喃鼠李糖三氯乙酰亚胺酯，这是由高度选择性3-O-获得酰化用作关键合成子，以得到所需的具有3 3-和3 7-游离羟基的α-（1→2）-和α-（1→3）连接的鼠李糖单糖受体。因此，合成了几种二糖，然后由它们合成了四糖和六糖。六糖供

  DOI：

  10.1016/s0040-4020(03)00075-9

文献信息

• Synthesis of β-d-GlcpNAc-(1→3)-α-l-Rhap-(1→2)-[β-l-Xylp-(1→4)]-α-l-Rhap-(1→3)-α-l-Rhap, the repeating unit of the O-antigen produced by Pseudomonas solanacearumICMP 7942
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00358-0

  日期：2003.1

  Abstract An efficient synthesis of β- d -Glc p NAc-(1→3)-α- l -Rha p -(1→2)-[β- l -Xyl p -(1→4)]-α- l -Rha p -(1→3)-α- l -Rha p , the repeating unit of the O-antigen produced by Pseudomonas solanacearum ICMP 7942 and its isomer β- d -Glc p NAc-(1→3)-α- l -Rha p -(1→4)-[β- l -Xyl p -(1→2)]-α- l -Rha p -(1→3)-α- l -Rha p was achieved via sequential assembly of the building blocks, allyl 2,3- O -isopropylidene-α-

  摘要β-d -Glc p NAc-（1→3）-α-l-Rha p-（1→2）-[β-l-Xyl p-（1→4）]-α-l的有效合成-Rha p-（1→3）-α-1-Rha p，是茄假单胞菌ICMP 7942及其异构体β-d -Glc p NAc-（1→3）-α-产生的O抗原的重复单元。 l -Rha p-（1→4）-[β-1-Xyl p-（1→2）]-α-l-Rha p-（1→3）-α-1-Rha p通过顺序组装得到的组成部分中，烯丙基2,3-O-异亚丙基-α-1-鼠李糖吡喃糖苷（2），烯丙基3,4-O-异亚丙基-α-1--1-鼠李糖吡喃糖苷（3），烯丙基2,4-二-O-苯甲酰基-α-1-鼠李糖吡喃糖苷（6），3,4,6-三-O-乙酰基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖基三氯乙酰亚胺酸酯（7），和2,3,4-三- O-苯甲酰基-β-1-木吡喃糖基三氯乙酰亚胺酸酯（12）。
• Synthesis of a group of diosgenyl saponins by a one-pot sequential glycosylation
  作者：Biao Yu、Hai Yu、Yongzheng Hui、Xiuwen Han

  DOI：10.1016/s0040-4039(99)01839-0

  日期：1999.12

  A group of natural diosgenyl saponins was synthesized in a highly efficient manner employing the 'one-pot sequential glycosylation' protocol with the combined use of glycosyl trichloroacetimidates and thioglycosides. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis of the tetrasaccharide outer core fragment of Burkholderia multivorans lipooligosaccharide
  作者：Marcello Ziaco、Cristina De Castro、Alba Silipo、Maria Michela Corsaro、Antonio Molinaro、Alfonso Iadonisi、Rosa Lanzetta、Michelangelo Parrilli、Emiliano Bedini

  DOI：10.1016/j.carres.2014.04.018

  日期：2015.2

  The first synthesis of the outer core fragment of Burkholderia multivorans lipooligosaccharide [beta-D-Glc-(1 -> 3)-alpha-D-GalNAc-(1 -> 3)-beta-D-GalNAc-(1 -> 3)-L-Rha] as alpha-allyl tetrasaccharide was accomplished. The glycosylations involving GalNAc units were studied in depth testing them under several conditions. This allowed the building of both the alpha- and the beta-configured glycosidic bonds by employing the same GalNAc glycosyl donor, thus considerably shortening the total number of synthetic steps. The target tetrasaccharide was synthesized with an allyl aglycone to allow its future conjugation with an immunogenic protein en route to the development of a synthetic neoglycoconjugate vaccine against the Burkholderia cepacia pathogens. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthetic oligorhamnans related to the most common O-chain backbone from phytopathogenic bacteria
  作者：Emiliano Bedini、Antonella Carabellese、Daniela Comegna、Cristina De Castro、Michelangelo Parrilli

  DOI：10.1016/j.tet.2006.06.084

  日期：2006.9

  The synthesis of the tetrasaccharide rhamnanic motif alpha-L-Rha-(1 -> 3)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha-(1 -> 2)-alpha-L-Rha and its dimerization to octasaccharide have been developed. Three different pathways toward the dimerization have been investigated; the best one was based on a [4+2]+2 stepwise condensation of a rhamnose tetrasaccharide with two rhamnosyl N-phenyl ttifluoroacetimidates as glycosyl donors and on an orthogonal set of protecting groups consisting of benzoyl, levulinoyl, and allyl groups. (c) 2006 Elsevier Ltd. All rights reserved.
• A concise synthesis of two isomeric pentasaccharides, the O repeat units from the lipopolysaccharides of P. syringae pv. porri NCPPB 3364T and NCPPB 3365
  作者：Zuchao Ma、Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/j.carres.2003.09.014

  日期：2004.1

  A concise synthesis of two isomeric pentasaccharides, alpha-L-Rhap-(1-->2)-alpha-L-Rhap-(1-->3)-alpha-L-Rhap-(1-->3)-[beta-D-GlcpNAc-(1--> 2)]-alpha-L-Rhap (A) and alpha-L-Rhap-(1-->2)-alpha-L-Rhap-(1-->3)-[beta-D-GlcpNAc-(1-->2)]-alpha-L-Rhap-(1-->3)-alpha-L-Rhap (B), the O repeats from the lipopolysaccharides of Pseudonomonas syringae pv. porri NCPPB 3364(T) and 3365 was achieved via assembly of the building blocks, allyl 3,4-di-O-benzoyl-alpha-L-rhamnopyranoside (1), 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate (2), allyl 4-O-benzoyl-3-O-chloroacetyl-alpha-L-rhamnopyranoside (6), 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate (7), and allyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (10). Coupling of 1 with 2 followed by deallylation and trichloroacetimidate formation gave the disaccharide donor 5, while condensation of 6 with 7, followed by dechloroacetylation, offered the disaccharide acceptor 9. Then, 5 was coupled with 10 to obtain the trisaccharide 11, and subsequent deallylation and trichloroacetimidate formation furnished the trisaccharide donor 13. Coupling of 9 with 13, followed by deprotection, afforded pentasaccharide 19, while condensation of 9 with 5, followed by deallylation and trichloroacetimidate formation, gave the tetrasaccharide donor 16, whose coupling with 10 and subsequent deprotection yielded another pentasaccharide 22. (C) 2003 Elsevier Ltd. All rights reserved.