p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside | 319922-17-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-(hydroxymethyl)-6-(4-methoxyphenoxy)-4-prop-2-enoxyoxane-3,5-diol
• CAS: 319922-17-3
• 化学式: C₁₆H₂₂O₇
• 分子量: 326.346
• InChiKey: DXDVGRALJDFCOJ-OWYFMNJBSA-N

物化性质

• 沸点：
  538.9±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.6
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 4-methoxyphenyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
  参考文献：
  名称：

  Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?

  摘要：

  Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-alpha -D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various accepters (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the p-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01497-0
• 作为产物：
  描述：

  1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 三氟甲磺酸 、 sodium methylate 、 二正丁基氧化锡 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside
  参考文献：
  名称：

  Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?

  摘要：

  Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-alpha -D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various accepters (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the p-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01497-0

文献信息

• Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3
  作者：Langqiu Chen、Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(02)00011-3

  日期：2002.3

  3- O -allyl-2,4,6-tri- O -benzoyl-α- d -mannopyranosyl trichloroacetimidate ( 5 ). Condensation of 5 with methyl 4,6- O -benzylidene-α- d -mannopyranoside ( 6 ) selectively afforded the (1→3)-linked disaccharide 7 . Benzoylation of 7 , debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri- O -benzoyl-α- d -mannopyranosyl-(1→3)-2,4,6-tri- O -benzoyl-α- d -mannopyranoside ( 11 ) as the

  摘要大肠杆菌O9a的四糖重复单元，α-d -Man p-（1→2）-α-d -Man p-（1→3）-α-d -Man p-（1→3）-d -Man p和大肠杆菌O9和克雷伯菌O3的五糖重复单元，α-d -Man p-（1→2）-α-d-Man p-（1→2）-α-d -Man p合成了-（1→3）-α-d-Manp-（1→3）-d-Man p作为甲基糖苷。因此，对-甲氧基苯基α-d-甘露吡喃糖苷经由二丁基锡中间体的选择性3-O-烯丙基化以良好的产率得到了对-甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（2）。苯甲酰化（→3），然后除去1- O-甲氧基苯基（→4），然后进行三氯乙酰亚胺化，得到3- O-烯丙基-2,4,6-三-O-苯甲酰基-α-d-甘露酰吡喃糖基三氯乙酰胺酸酯（5 ）。5与甲基4,6-O-亚苄基-α-d-甘露吡喃糖苷（6）缩合选择性地提供（1→3）-连接的二糖7。7的苄基
• AN EFFICIENT AND PRACTICAL SYNTHESIS OF α-(1→3)-LINKED MANNOHEXAOSE AND MANNOOCTAOSE
  作者：Langqiu Chen、Fanzuo Kong

  DOI：10.1081/car-120014899

  日期：2002.1.10

  tetrasaccharide 22, respectively. The tetrasaccharide 20 was prepared from oxidative cleavage of 1-O-p-methoxyphenyl of 19, which was obtained from coupling of 9 with 11. The tetrasaccharide 22 was obtained from condensation of the donor 13 with the acceptor 18. These disaccharides 9, 11, 13, and 18 were produced easily by simple chemical transformation using p-methoxyphenyl 3-O-allyl-α-d-mannopyranoside (1) and

  α-（1→3）-连接的甘露六糖和甘露糖八糖作为其甲基糖苷是由相应的α-（1→3）-连接的二-（9）和四糖供体（21）与四糖受体（23）缩合而合成的分别进行脱酰作用。分别通过激活四糖20的C-1和四糖22的脱甲酰作用容易地制备供体21和受体23。通过将9与11偶联获得的19的1-Op-甲氧基苯基的氧化裂解制备四糖20。通过供体13与受体18的缩合获得四糖22。这些二糖9、11、13 ，使用对甲氧基苯基3-O-烯丙基-α-d-甘露吡喃糖苷（1）和2,3,4通过简单的化学转化即可轻松制得18和
• Synthesis of the ‘primer–adaptor’ trisaccharide moiety of Escherichia coli O8, O9, and O9a lipopolysaccharide
  作者：Chunjuan Liu、Fredrik Skogman、Ye Cai、Todd L. Lowary

  DOI：10.1016/j.carres.2007.08.020

  日期：2007.12

  Described is the synthesis of the trisaccharide alpha-D-Manp-(1-->3)-alpha-D-Manp-(1-->3)-beta-D-GlcpNAcO(CH2)(8)N-3, the glycan portion of which corresponds to the 'adaptor-primer' moiety linking the O-chain and core oligosaccharide in the lipopolysaccharide of several Escherichia coli and Klebsiella pneumoniae serotypes. This report represents the first synthesis of this trisaccharide motif, and in the route involved, a key step is a [2+1] coupling of a protected Manp-(1-->3)-alpha-D-Manp glycosyl donor with a GlcpNAc acceptor. The azido group was included in the target to facilitate future preparation of neoglycoconjugates. (C) 2007 Elsevier Ltd. All rights reserved.
• Can preferential β-mannopyranoside formation with 4,6-O-benzylidene protected mannopyranosyl sulfoxides be reached with trichloroacetimidates?
  作者：Ralf Weingart、Richard R Schmidt

  DOI：10.1016/s0040-4039(00)01497-0

  日期：2000.11

  Studies with 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-alpha -D-mannopyranosyl sulfoxide (3d) and the corresponding trichloroacetimidate (4) as glycosyl donors and various accepters (A-F) led under similar reaction conditions to similar glycosylation results, i.e. mainly or exclusively the p-anomers of glycosides 5dA-5dF could be obtained. Thus, the versatile building block 5dA for N-glycan synthesis is readily available. For the activation of the sulfoxide leaving group, one equivalent of Tf2O and two equivalents of DTBMP are required, whereas for trichloroacetimidate activation catalytic amounts of TMSOTf are sufficient; hence, the trichloroacetimidate based procedure is very convenient. Various parameters were modified in the reaction of 4 with A (catalyst concentration, configuration of 4, size of the 2-O-protective group, solvent), thus, a proposal for the reaction course was derived. (C) 2000 Elsevier Science Ltd. All rights reserved.