2,3,5-tri-O-benzyl-β-D-ribofuranosyl trichloroacetimidate | 284036-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,5-tri-O-benzyl-β-D-ribofuranosyl trichloroacetimidate
• 英文别名: Bn(-2)[Bn(-3)][Bn(-5)]Ribf(b)-O-C(NH)CCl3；[(2S,3R,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl] 2,2,2-trichloroethanimidate
• CAS: 284036-78-8
• 化学式: C₂₈H₂₈Cl₃NO₅
• 分子量: 564.893
• InChiKey: AUJCRDYIYKUEDD-POTDNYQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzyl-β-D-ribofuranosyl trichloroacetimidate 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 α-D-ribofuranosyl methylphosphonate
  参考文献：
  名称：

  A concise synthesis of α-D-ribofuranosyl alkylphosphonates — Putative substrate intermediates for the carbon–phosphorous lyase system

  摘要：

  碳磷裂解酶是一种存在于多种细菌中的多酶系统，其特点是能够水解多种未活化的烷基膦酸盐。α-D-Ribofuranosyl 烷基膦酸盐是碳磷裂解酶途径产生的潜在代谢中间产物。关键词：碳磷裂解酶；phn操作子；phnN；膦酸盐；三氯乙酰亚氨酸糖基供体；α-D-核呋喃糖基乙基膦酸盐。

  DOI：

  10.1139/v06-038
• 作为产物：
  描述：

  2,3,5-三-O-苄基呋喃戊糖 、 三氯乙腈 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2,3,5-tri-O-benzyl-β-D-ribofuranosyl trichloroacetimidate
  参考文献：
  名称：

  A concise synthesis of α-D-ribofuranosyl alkylphosphonates — Putative substrate intermediates for the carbon–phosphorous lyase system

  摘要：

  碳磷裂解酶是一种存在于多种细菌中的多酶系统，其特点是能够水解多种未活化的烷基膦酸盐。α-D-Ribofuranosyl 烷基膦酸盐是碳磷裂解酶途径产生的潜在代谢中间产物。关键词：碳磷裂解酶；phn操作子；phnN；膦酸盐；三氯乙酰亚氨酸糖基供体；α-D-核呋喃糖基乙基膦酸盐。

  DOI：

  10.1139/v06-038

文献信息

• Direct <i>N</i>-glycosylation of tosyl and nosyl carbamates with trichloroacetimidate donors
  作者：Ariza Khanam、Pintu Kumar Mandal

  DOI：10.1039/d1nj02051j

  日期：——

  Acidic sulphonamide reactants act as both catalysts and nucleophiles to afford the desired N-glycofuranosyl sulfonamides stereoselectively.

  酸性磺胺反应物既充当催化剂又作为亲核试剂，从而选择性地生成所需的N-糖呋喃基磺胺。
• Synthesis of Oxaphosphinane-Based Pseudodisaccharides
  作者：Rachida Babouri、Ludovic Clarion、Marc Rolland、Arie Van der Lee、Zahia Kabouche、Jean-Noël Volle、David Virieux、Jean-Luc Pirat

  DOI：10.1002/ejoc.201700878

  日期：2017.10.2

  The synthesis of pseudodisaccharides based on an oxaphosphinane heterocycle is described. Disaccharide mimetics 5 and 6 were readily obtained through glycosylation of a hydroxy group with appropriately protected furanosyl or pyranosyl carbohydrates using a trichloroacetamidate coupling strategy. Selective or complete deprotection then produced the chiral pseudodisaccharides in good yields.

  描述了基于氧杂膦杂环的假二糖的合成。使用三氯乙酰胺酸酯偶联策略，通过羟基与适当保护的呋喃糖基或吡喃糖基碳水化合物进行糖基化，很容易获得二糖模拟物 5 和 6。选择性或完全脱保护然后以良好的产率产生手性假二糖。
• Base- and Sugar-Modified Cytidine MonophosphateN-Acetylneuraminic Acid (CMP-Neu5Ac) Analogues - Synthesis and Studies with α(2-6)-Sialyltransferase from Rat Liver
  作者：Gesche Dufner、Ralf Schwörer、Bernd Müller、Richard R. Schmidt

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1467::aid-ejoc1467>3.0.co;2-e

  日期：2000.4

  The reaction of sialyl phosphites 1, 22a-d, 28, 39, and 45 with acyl-protected riboside 5-phosphorous acids 2a,b and 23 directly furnished, without addition of a catalyst, under phosphite/phosphate exchange the corresponding beta-configured sialyl riboside monophosphates 3a,b, 24a-d, 29, 46, and 47. The synthesis of the starting materials, formation of the products, and their treatment with sodium methanolate in methanol and subsequent hydrolysis of the sialic acid ester moiety to provide the unprotected target molecules 4a,b, 25a-d, 30, 48, and 49 is described. Investigations with alpha(2-6)-sialyl-transferase from rat Liver showed that base replacement in CMP-Neu5Ac (4a,b) is not tolerated by the enzyme but that modifications of the 5-, 8-, or g-position of the neuraminic acid residue (25a-d, 30, 48, 49) are tolerated.
• A concise synthesis of α-<scp>D</scp>-ribofuranosyl alkylphosphonates — Putative substrate intermediates for the carbon–phosphorous lyase system
  作者：Yan Luo、David L Zechel

  DOI：10.1139/v06-038

  日期：2006.4.1

  Carbon–phosphorous lyase is a multienzyme system found in many species of bacteria that is distinguished by its ability to hydrolyze a broad array of unactivated alkylphosphonates. α-D-Ribofuranosyl alkylphosphonates are potential metabolic intermediates generated by the carbon–phosphorous lyase pathway. Here we describe a facile synthesis of α-D-ribofuranosyl alkylphosphonates using β-D-ribofuranosyl trichloracetimidate as a glycosyl donor.Key words: carbon–phosphorous lyase, phn operon, phnN, phosphonates, glycosyl trichloroacetimidate donor, α-D-ribofuranosyl ethylphosphonate.

  碳磷裂解酶是一种存在于多种细菌中的多酶系统，其特点是能够水解多种未活化的烷基膦酸盐。α-D-Ribofuranosyl 烷基膦酸盐是碳磷裂解酶途径产生的潜在代谢中间产物。关键词：碳磷裂解酶；phn操作子；phnN；膦酸盐；三氯乙酰亚氨酸糖基供体；α-D-核呋喃糖基乙基膦酸盐。