allyl 4-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside | 541503-00-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 4-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside
• 英文别名: [(2S,3S,4S,5R,6R)-4-(2-chloroacetyl)oxy-5-hydroxy-2-methyl-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 541503-00-8
• 化学式: C₁₈H₂₁ClO₇
• 分子量: 384.814
• InChiKey: LQYWRKCRYKPYLG-MMKGNIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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 4-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranoside 在 吡啶 、 sodium acetate 、 溶剂黄146 、 palladium dichloride 作用下， 反应 12.0h， 生成 2,4-di-O-benzoyl-3-O-chloroacetyl-L-rhamnopyranose
  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
• 作为产物：
  描述：

  allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside 在 吡啶 、 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 27.0h， 生成 allyl 4-O-benzoyl-3-O-chloroacetyl-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 a hexasaccharide fragment of group E streptococci polysaccharide and the tetrasaccharide repeating unit of E. coli O7:K98:H6
  作者：Youlin Zeng、Fanzuo Kong

  DOI：10.1016/j.carres.2004.03.027

  日期：2004.6

  Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli 07:K98:H6, were achieved by constructing alternate alpha-L-(l --> 2)- and alpha-L-(1 --> 3)linked L-rhamnopyranose backbones and substituting with beta-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 Elsevier Ltd. All rights reserved.Syntheses of a hexasaccharide, the dimer of the repeating unit of the group E streptococci polysaccharide, and a tetrasaccharide, the repeating unit of the E. coli O7:K98:H6, were achieved by constructing alternate alpha-L-(1 --> 2)- and alpha-L-(1 --> 3)-linked L-rhamnopyranose backbones and substituting with P-linked D-glucopyranose side chains for the former, and a D-gluco-pyranosyluronate branch for the latter, respectively, at O-2 of the L-rhamnose ring. (C) 2004 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.
• A general method for the synthesis of oligosaccharides consisting of α-(1→2)- and α-(1→3)-linked rhamnan backbones and GlcNAc side chains
  作者：Jianjun Zhang、Fanzuo Kong

  DOI：10.1016/s0040-4020(03)00075-9

  日期：2003.2

  and 3-O-acetyl-2,4-di-O-benzoyl-α-l-rhamnopyranosyl trichloroacetimidate, which were obtained by highly regioselective 3-O-acylations, were used as the key synthons to obtain the required α-(1→2)- and α-(1→3)-linked rhamnoocta saccharide acceptors with 33- and 37-free hydroxyl groups. Therefore, several disaccharides were synthesized, from which tetrasaccharides and hexasaccharides were then synthesized

  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