[(2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] 2,2,2-trichloroethanimidate | 319922-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: [(2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] 2,2,2-trichloroethanimidate
• CAS: 319922-26-4
• 化学式: C₂₅H₂₆Cl₃NO₆
• 分子量: 542.844
• InChiKey: OTGSKULXNYIBJF-WSJQOYCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] 2,2,2-trichloroethanimidate 在 吡啶 、 4-二甲氨基吡啶 、 硼烷四氢呋喃络合物 、 trans-[Pd(NH₂)2Cl₂] 、 三氟甲磺酸三甲基硅酯 、 HP*pyridine 、 三氟甲磺酸二丁硼 、 sodium hydride 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.33h， 生成 O-[2,4-di-O-benzyl-6-O-(9-fluorenylmethoxycarbonyl)-3-O-phenoxyacetyl-β-D-mannopyranosyl]-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  固相合成新型寡糖的封端试剂。

  摘要：

  报道了核心N-聚糖四糖和含有加利利抗原的三糖的固相支持的寡糖合成。合成基于连接到Merrifield树脂的羟甲基苄基苯甲酸酯间隔基-接头系统，O -Fmoc保护的O-糖基三氯乙酰亚氨酸酯作为糖基供体，以及苯甲酰基异氰酸酯作为低反应性羟基的封端剂。以这种方式，可以有效地获得目标分子而几乎没有副产物形成，因此最终纯化是方便的。

  DOI：

  10.1021/jo0354239
• 作为产物：
  描述：

  (2R,4aR,6R,7S,8R,8aR)-8-Allyloxy-6-(4-methoxy-phenoxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 cerium(III) ammonium nitrate 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [(2R,4aR,6R,7S,8S,8aR)-2-phenyl-7-phenylmethoxy-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl] 2,2,2-trichloroethanimidate
  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

• Solid-Phase Synthesis of Complex Oligosaccharides Using a Novel Capping Reagent
  作者：Xiangyang Wu、Richard R. Schmidt

  DOI：10.1021/jo0354239

  日期：2004.3.1

  Solid-phase-supported oligosaccharide synthesis of a core N-glycan tetrasaccharide and of a trisaccharide containing the Galili antigen is reported. The synthesis is based on a hydroxymethylbenzyl benzoate spacer−linker system attached to the Merrifield resin, O-Fmoc-protected O-glycosyl trichloroacetimidates as glycosyl donors, and benzoyl isocyanate as a capping reagent for low-reactivity hydroxy

  报道了核心N-聚糖四糖和含有加利利抗原的三糖的固相支持的寡糖合成。合成基于连接到Merrifield树脂的羟甲基苄基苯甲酸酯间隔基-接头系统，O -Fmoc保护的O-糖基三氯乙酰亚氨酸酯作为糖基供体，以及苯甲酰基异氰酸酯作为低反应性羟基的封端剂。以这种方式，可以有效地获得目标分子而几乎没有副产物形成，因此最终纯化是方便的。
• 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.