4-methoxyphenyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside | 319922-22-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxyphenyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside
• CAS: 319922-22-0
• 化学式: C₃₀H₃₂O₇
• 分子量: 504.58
• InChiKey: ACACVISMIMMNCY-FBLDLFPLSA-N

物化性质

• 沸点：
  635.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.07
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  4-methoxyphenyl 3-O-allyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 在 三氟甲磺酸三甲基硅酯 、 cerium(III) ammonium nitrate 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成
  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：

  4-甲氧苯基-Alpha-D-吡喃甘露糖苷 在 sodium hydride 、 二正丁基氧化锡 、 对甲苯磺酸 作用下， 以 甲醇 、 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

文献信息

• Protection of Hydroxy Groups with Diphenylmethyl and 9-Fluorenyl Trichloroacetimidates− Effect on Anomeric Stereocontrol
  作者：Ibrahim A. I. Ali、El Sayed H. El Ashry、Richard R. Schmidt

  DOI：10.1002/ejoc.200300323

  日期：2003.11

  protection of alcohols. The compatibility of these groups with other chemical manipulations is demonstrated. Glucosylation of typical acceptors with an O-glucopyranosyl trichloroacetimidate as donor having a DPM group at 2-O afforded β-glucopyranosides, thus demonstrating anchimeric assistance of the DPM group in the anomeric stereocontrol. This effect was also observed in mannopyranoside synthesis. (©

  使用 O-二苯基甲基 (DPM) 和 O-(9-芴基) (Fl) 三氯乙酰亚胺可以有效保护醇。证明了这些基团与其他化学操作的兼容性。典型受体与 O-吡喃葡萄糖基三氯乙酰亚胺酯作为供体的葡萄糖基化，在 2-O 处具有 DPM 基团，提供 β-吡喃葡萄糖苷，从而证明 DPM 基团在异头立体控制中的嵌合辅助。在吡喃甘露糖苷合成中也观察到这种效应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)