(2'RS)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose | 27994-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'RS)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose
• 英文别名: 3-O-[2',3'-anhydropropyl]-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；3-O-(2' ,3'-epoxypropyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；O¹,O²;O⁵,O⁶-diisopropylidene-O³-(Ξ)-oxiranylmethyl-α-D-glucofuranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-(oxiran-2-ylmethoxy)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 27994-41-8
• 化学式: C₁₅H₂₄O₇
• 分子量: 316.351
• InChiKey: UJYWGCVKPNGAIK-ZVACVBPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2'RS)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose 在 盐酸 、 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 (2'RS)-1,2-O-isopropylidene-3-O-[3'-(N,N-dimethylamino)-2'-hydroxy-propan-1'-yl]-α-D-glucofuranose
  参考文献：
  名称：

  Syntheses and immunomodulatory activity of 3-O-[2′-hydroxy-3′-N,N-disubstituted aminopropan-1′-yl]-α-d-glucofuranoses

  摘要：

  A number of 3-O-[2 ' -hydroxy-3 ' -N,N-aminopropan-l ' -yl]-alpha -D-glucofuranoses were synthesised by regioselective oxirane ring opening in compound 2 with different secondary amines followed by selective deacetalisation. All the compounds were tested for their immunomodulatory potential in vitro; seven of them expressed significant immunostimulant activity. (C) 2001 Editions scientifiques et medicales Elsevier SAS.

  DOI：

  10.1016/s0223-5234(01)01234-x
• 作为产物：
  描述：

  二氧化硅 在 硫酸 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2'RS)-1,2,5,6-di-O-isopropylidene-3-O-[2',3'-epoxypropan-1'-yl]-α-D-glucofuranose
  参考文献：
  名称：

  Synthesis and characterization of a new methacrylic glycomonomer

  摘要：

  以 D-葡萄糖和甲基丙烯酸为原料，通过 4 个步骤轻松制备出了含碳水化合物的单体 3-O-（2'-羟基-3'-甲基丙烯酰氧基丙基）-1,2:5,6-二-O-异亚丙基-α-D-呋喃葡萄糖。 利用傅立叶变换红外光谱、核磁共振（包括 ^1H-NMR、^{13}C-NMR、COSY、HMQC 和 HMBC）和 HPLC-MS 确认了新的甲基丙烯酸单体的结构。这项工作是我们研究小组为获得基于可再生资源、具有更强生物降解性和生物相容性的新型聚合物所做努力的一部分。

  DOI：

  10.3906/kim-1103-63

文献信息

• [EN] POLYPEPTIDES, PEPTIDES, AND PROTEINS FUNCTIONALIZED BY ALKYLATION OF THIOETHER GROUPS VIA RING-OPENING REACTIONS<br/>[FR] POLYPEPTIDES, PEPTIDES ET PROTÉINES FONCTIONNALISÉ(E)S PAR ALKYLATION DE GROUPES THIOÉTHER VIA DES RÉACTIONS D'OUVERTURE DE CYCLE
  申请人：UNIV CALIFORNIA

  公开号：WO2016154120A1

  公开（公告）日：2016-09-29

  Some embodiments of the invention involve methods for introduction of various functional groups onto polypeptides, peptides and proteins by alkylation of thioether (a.k.a. sulfide) groups by ring opening reactions, creating new compositions of matter that may be useful for medical therapeutic or diagnostic applications. The thioether groups may either be present in the polypeptides, or may be added to polypeptides by chemical modification, such as by alkylation of thiol (sulfhydryl) groups.

  该发明的一些实施例涉及通过开环反应烷基化硫醚（又称硫化物）基团，将各种功能基团引入多肽、肽和蛋白质的方法，从而创造可能对医学治疗或诊断应用有用的新物质组合。这些硫醚基团可以存在于多肽中，也可以通过化学修饰（例如通过烷基化巯基（巯基）基团）添加到多肽中。
• Oxirane ring-opening reactions of 3-O-(2,3-epoxypropyl)-1,2:5,6-DI-O-isopropylidene-α-d-glucofuranose
  作者：R.E. Wing、W.M. Doane、C.E. Rist

  DOI：10.1016/s0008-6215(00)80615-1

  日期：1970.3

  Abstract Reactions are reported of the oxirane ring of 3- O -(2,3-epoxypropyl)-1,2:5,6-di- O -isopropylidene-α- d -glucofuranose with water, primary and secondary alcohols, lithium aluminum hydride, ammonia, primary and secondary amines, and dipotassium hydrogen phosphate. In most reactions, the expected products were obtained in quantitative yields.

  摘要报道了3- O-（2,3-环氧丙基）-1,2：5,6-二-O-异亚丙基-α-d-葡糖呋喃糖的环氧乙烷环与水，伯醇和仲醇，锂铝的反应氢化物，氨，伯胺和仲胺以及磷酸氢二钾。在大多数反应中，预期产物以定量产率获得。
• Polypeptides, peptides, and proteins functionalized by alkylation of thioether groups via ring-opening reactions
  申请人：The Regents of the University of California

  公开号：US10351591B2

  公开（公告）日：2019-07-16

  Some embodiments of the invention involve methods for introduction of various functional groups onto polypeptides, peptides and proteins by alkylation of thioether (a.k.a. sulfide) groups by ring opening reactions, creating new compositions of matter that may be useful for medical therapeutic or diagnostic applications. The thioether groups may either be present in the polypeptides, or may be added to polypeptides by chemical modification, such as by alkylation of thiol (sulfhydryl) groups.

  本发明的一些实施方案涉及通过开环反应将硫醚（又称硫化物）基团烷基化，将各种官能团引入多肽、肽和蛋白质的方法，从而产生可用于医疗或诊断应用的新物质组合物。硫醚基团既可以存在于多肽中，也可以通过化学修饰（如硫醇（巯基）的烷基化）添加到多肽中。
• Synthesis of Phenylseleno Sugars from Epoxides and of α,β‐Unsaturated Carbonyl Derivatives for the Study of Their Insecticidal Activity
  作者：Amélia P. Rauter、Tana Canda、Jorge Justino、Maria I. Ismael、José A. Figueiredo

  DOI：10.1081/car-200030077

  日期：2004.12.29

  This work reports the synthesis of sugar epoxides and their derivatives obtained by reaction with the dianion of phenyl selenoacetic acid. Approaches to the introduction of alpha,beta-unsaturated carbonyl units in pyranoid systems were investigated. Preparation of a protected D-glycero-hex-3-enepyranosid-2-ulose and of a D-erythro-hex-2-enono-1,5-lactone is described. Some of the synthesized compounds possess insecticidal activity against fruit flies, house flies, and white flies.
• POLYPEPTIDES, PEPTIDES, AND PROTEINS FUNCTIONALIZED BY ALKYLATION OF THIOETHER GROUPS VIA RING-OPENING REACTIONS
  申请人：The Regents of the University of California

  公开号：US20180105553A1

  公开（公告）日：2018-04-19

  Some embodiments of the invention involve methods for introduction of various functional groups onto polypeptides, peptides and proteins by alkylation of thioether (a.k.a. sulfide) groups by ring opening reactions, creating new compositions of matter that may be useful for medical therapeutic or diagnostic applications. The thioether groups may either be present in the polypeptides, or may be added to polypeptides by chemical modification, such as by alkylation of thiol (sulfhydryl) groups.