allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 120142-50-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside；allyl 4,6-O-benzylidine-2-deoxy-2-phthalimido-β-D-glucopyranoside；2-[(2R,4aR,6R,7R,8R,8aS)-8-hydroxy-2-phenyl-6-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• CAS: 120142-50-9
• 化学式: C₂₄H₂₃NO₇
• 分子量: 437.449
• InChiKey: WICBVZCYSYXMJM-RHEDTODXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 吡啶 、 盐酸 、 三氟甲磺酸三甲基硅酯 、 sodium cyanoborohydride 作用下， 生成 [(2R,3S,4R,5R,6R)-3-[(2S,3R,4R,5S,6R)-4-acetyloxy-5-[tert-butyl(dimethyl)silyl]oxy-3-(1,3-dioxoisoindol-2-yl)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-5-(1,3-dioxoisoindol-2-yl)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-4-yl] acetate
  参考文献：
  名称：

  Lamberth, Clemens; Nagy, Jon O.; Kasper, Cornelia, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 819 - 824

  摘要：

  DOI：
• 作为产物：
  描述：

  2-脱氧-2-苯二酰亚胺-1,3,4,6-四-氧-乙酰-β-D-吡喃葡萄糖 在 盐酸 、 氢溴酸 、 氰化汞 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 丙酮 为溶剂， 生成 allyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Lamberth, Clemens; Nagy, Jon O.; Kasper, Cornelia, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 5, p. 819 - 824

  摘要：

  DOI：

文献信息

• Bimodal Glycosyl Donors Protected by 2-<i>O-</i>(<i>ortho</i>-Tosylamido)benzyl Group
  作者：Feiqing Ding、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1021/acs.orglett.8b01922

  日期：2018.7.20

  A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf2NH. On the other hand, activation by TfOH in Et2O provided α-glycosides as major products. This “single donor” approach was employed to assemble naturally

  通过改变反应条件，显示了配备有C 2 -o- TsNH苄基醚的葡糖基供体同时提供α-和β-糖苷的立体选择性。即，当通过Tf 2 NH激活三氯乙酰亚胺酸酯时，选择性地获得β-糖苷。另一方面，通过TfOH在Et 2 O中的活化提供了α-糖苷作为主要产物。这种“单一供体”的方法被用来装配自然三糖α-发生d -Glc-（→2 1）-α- d -Glc-（1→6） - d -Glc和它的端基异构体。
• Efficient one-pot per-O-acetylation–thioglycosidation of native sugars, 4,6-O-arylidenation and one-pot 4,6-O-benzylidenation–acetylation of S-/O-glycosides catalyzed by Mg(OTf)₂
  作者：Mana Mohan Mukherjee、Nabamita Basu、Aritra Chaudhury、Rina Ghosh

  DOI：10.1039/c6ra23198e

  日期：——

  A sequential one-pot per-O-acetylation–S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated

  据报道，在无溶剂条件下，使用0.5摩尔％的Mg（OTf）2作为非吸湿性，可循环利用的催化剂，对单糖和双糖进行连续一锅过O-乙酰化– S- / O-糖基化反应。糖苷和硫糖苷与苯甲醛或对甲氧基苯甲醛二甲基乙缩醛的区域选择性4,6- O-芳基化反应可通过10摩尔％的Mg（OTf）2催化生成相应的4,6- O-芳基化产物。Mg（OTf）2也可以高产率地介导单糖和二糖基糖苷和硫代糖苷的顺序一锅苯甲基化-乙酰化。
• Synthesis and characterisation of muramic acid 1′,2-lactam-β-(1→4)-d-glucosamine derivatives related to repeating units of bacterial spore cortex
  作者：Dina Keglevic、Biserka Kojić-Prodic、Zrinka Banic Tomišic、Anthony L. Spek

  DOI：10.1016/s0008-6215(98)00248-1

  日期：1998.11

  -benzyl-2-deoxy- β - d -glucopyranoside. The conformation analysis of allyl 4,6- O -benzylidene-muramic acid δ -lactam and propan-2-onyl glycoside of the protected muramic ester revealed in solid state for both compounds a chair conformation of glucopyranose and 1,3-dioxane rings with trans ring junction. The δ -lactam ring of the tricyclic muramyl lactam exhibits a conformation between sofa and half-chair .

  摘要描述了一种制备4，6-O-亚苄基-N-邻苯二甲酰基-山酰胺酸烯丙基甲基酯的方法。取决于反应条件，还发生了邻苯二甲酰基的部分裂解和三环烯丙基4，6-O-亚苄基-山酰胺酸1'，2-内酰胺的形成；后者的成功途径是通过保护的村mic酸酯基团的去酯化（LiI），去邻苯二甲酰化和环化。通过X射线结构分析表征该化合物。用氯化三（三苯基膦）铑（I）处理受保护的山梨酸酯，得到所需的半缩醛，然后将其转化为三氯乙酰亚胺供体，并与烯丙基3,6-二-O-苄基-2-脱氧-2-邻苯二甲酰亚胺基偶联。 -β-d-吡喃葡萄糖苷提供烯丙基O-（4，6-O-亚苄基-2-脱氧-3-O-[（R）-1-（甲氧羰基）乙基] -2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖基）-（1→4）-3,6-di- O-苄基-2-脱氧-2-邻苯二甲酰亚胺基-β-d-吡喃葡萄糖苷。脱酯化，然后除去两个邻苯二甲酰亚胺基团并进行Ac 2 O / Py处理，得到烯丙基O-（2-氨基-4
• Synthesis of a tetrasaccharide fragment of the circulating anodic antigen of Schistosoma mansoni
  作者：Koen M. Halkes、Ted M. Slaghek、Henricus J. Vermeer、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/0040-4039(95)01162-b

  日期：1995.8

  A stereocontrolled synthesis of the allyl glycoside of a tetrasaccharide fragment of the O-linked polysaccharide chain of the circulating anodic antigen of Schistosoma mansoni, beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc, is presented.
• Preparation of spacer-containing di-, tri-, and tetrasaccharide fragments of the circulating anodic antigen of Schistosoma mansoni for diagnostic purposes
  作者：Koen M Halkes、Henricus J Vermeer、Ted M Slaghek、Peter A.V van Hooft、Arnoud Loof、Johannis P Kamerling、Johannes F.G Vliegenthart

  DOI：10.1016/s0008-6215(98)00125-6

  日期：1998.5

  The chemical synthesis of beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2, and beta-D-GlcpA-(1 --> 3)-beta-D-GalpNAc-(1 --> 6)-[beta-D-GlcpA-(1 --> 3)]-beta-D-GalpNAc-(1 --> O)CH2CH = CH2 is described. These oligosaccharides represent fragments of the circulating anodic antigen, secreted by the parasite Schistosoma mansoni in the circulatory system of the host. The applied synthesis strategy includes the preparation of a non-oxidised backbone oligosaccharide, with a levulinoyl group at O-6 of the beta-D-glucose residue. After the selective removal of the levulinoyl group, the obtained hydroxyl functions were converted into carboxyl groups, using pyridinium dichromate and acetic anhydride in dichloromethane, to afford the desired glucuronic-acid-containing oligosaccharides. Subsequently, the allyl glycosides have been elongated with cysteamine to give the corresponding aminespacer-containing oligosaccharides. (C) 1998 Elsevier Science Ltd. All rights reserved.