1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate) | 65914-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate)
• 英文别名: 1,4,6-tri-O-acetyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside；1,4,6-tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose；Tri-O-acetyl pseudoglucal；tri-O-acetyl-D-glucal；tri-O-acetyl-D-glucan；tri-O-acetyl-2,3-dideoxy-ξ-D-erythro-hex-2-enopyranose；D-erythro-Hex-2-enopyranose, 2,3-dideoxy-, 1,4,6-triacetate；[(2R,3S)-3,6-diacetyloxy-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 65914-22-9
• 化学式: C₁₂H₁₆O₇
• 分子量: 272.255
• InChiKey: URHLHNBYVSNLQW-WIKAKEFZSA-N

物化性质

• 沸点：
  346.0±42.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate) 在 水 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 isopropyl 2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Di(2-pyridyl) carbonate promoted alkoxycarbonylation of amines: A convenient synthesis of functionalized carbamates

  摘要：

  The reaction of di(2-pyridyl) carbonate with a variety of alcohols including hindered secondary, tertiary and protected glycols afforded the corresponding mixed carbonate which was efficiently transformed into various carbamates in high yield under mild conditions.

  DOI：

  10.1016/s0040-4039(00)92141-5
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-D-glucal 在 nickel dichloride 、 nickel(I) chloride 作用下， 以 乙酸酐 为溶剂， 反应 13.0h， 生成 1,4,6-Tri-O-acetyl-α,β-D-erythro-hex-2-enopyranose (Pseudo-C-glucal triacetate)
  参考文献：
  名称：

  Inaba, Kiyoshi; Matsumura, Shuichi; Yoshikawa, Sadao, Chemistry Letters, 1991, # 3, p. 485 - 488

  摘要：

  DOI：

文献信息

• Allylic substitutions in tri-O-acetyl-glycals and related compounds
  作者：R.D. (Gus) Guthrie、Robert W. Irvine

  DOI：10.1016/s0008-6215(00)85698-0

  日期：1980.7

  Abstract The reaction of tri-O-acetyl- d -allal or - d -glucal, ethyl 4,6-di-O-acetyl-2,3-dideoxy-α- d )-erythro-hex-2-enopyranoside, or 1,4,6-tri-O-acetyl-α,β- d -erythro-hex-2-enopyranose with sodium azide in acetonitrile under catalysis by boron trifluoride diethyl etherate yields a mixture of 4,6-di-O-acetyl-3-azido-3-deoxy- d -allal and - d -glucal, together with both anomers of 4,6-di-O-acetyl-2

  摘要三-O-乙酰基-d-烯丙基或-d-葡糖醛，乙基4,6-二-O-乙酰基-2,3-二脱氧-α-d）-赤-己二-2-烯吡喃糖苷的反应三氟化硼二乙基乙醚化物催化下的1,4,6-三-O-乙酰基-α，β-d-赤型-己基-2-烯吡喃糖与叠氮化钠在乙腈中的反应生成4,6-二-O-乙酰基的混合物-3-azido-3-deoxy-d-alal和-d-glucal，以及4,6-di-O-乙酰基-2,3-dideoxy-d-erythro-hex-2-enopyranosyl azide的两种异构体。讨论了这些反应的机理。描述了3-氨基-3-脱氧-d-烯丙基和-d-葡糖醛及其衍生物。
• Synthesis of C 3 -Neoglycosides of digoxigenin and their anticancer activities
  作者：Xiao-san Li、Yi-chang Ren、Yu-zhou Bao、Jie Liu、Xiao-kun Zhang、You-wei Zhang、Xue-Long Sun、Xin-sheng Yao、Jin-Shan Tang

  DOI：10.1016/j.ejmech.2017.12.086

  日期：2018.2

  Cardiac glycosides exhibit significant anticancer effects and the glycosyl substitution at C3 position of digoxigenin is pivotal for their biological activity. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and explore more potent anticancer agents, a series of C3-O-neoglycosides and C3-MeON-neoglycosides of digoxigenin were synthesized by the Koenigs-Knorr

  心脏苷显示出显着的抗癌作用，洋地黄毒苷C 3位的糖基取代对其生物活性至关重要。为了研究强心苷的朝向癌症结构-活性关系（SAR）和探索更有效的抗癌剂，一系列的C 3 - ö -neoglycosides和C 3 -MeO Ñ -neoglycosides洋地黄毒苷的由合成的Koenigs-克诺尔和新糖基化方法。此外，地高辛通过高碘酸钠（NaIO 4）氧化和6-氨基己酸水解，从地高辛制备了洋地黄毒苷双指氧苷和单指氧苷。SAR分析表明C 3 - O洋地黄毒苷的β-新糖苷比C 3 -MeO N-新糖苷显示出更强的细胞毒性和对肿瘤细胞Nur77表达的诱导。另外，3 β - ö -glycosides显示比3更强的抗癌作用α - Ö -glycosides。其中，3 β - ø - （β -升-fucopyranosyl）-digoxigenin（3I）显示出对Nur77表达和转从细胞核至细胞质的诱导最高活性，导致癌细胞凋亡。
• NOVEL VASCULAR LEAKAGEAGE INHIBITOR
  申请人：Industry-Academic Cooperation Foundation, Yonsei University

  公开号：US20140378399A1

  公开（公告）日：2014-12-25

  The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present invention inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, and enhances the cortical actin ring structure, thereby inhibiting vascular leakage. Accordingly, the vascular leakage inhibitor of the present invention can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present invention is synthesized from commercially available or easily synthesizable pregnenolones, it has remarkably superior feasibility of commercial synthesis.

  本公开涉及一种新型血管渗漏抑制剂。本发明的新型血管渗漏抑制剂抑制血管内皮细胞凋亡，抑制由VEGF诱导的肌动蛋白应激纤维的形成，并增强皮质肌动蛋白环结构，从而抑制血管渗漏。因此，本发明的血管渗漏抑制剂可以预防或治疗由血管渗漏引起的各种疾病。由于本发明的血管渗漏抑制剂是由商业可获得或易于合成的孕酮合成的，因此具有明显优越的商业合成可行性。
• A one-step C-linked disaccharide synthesis from carbohydrate allylsilanes and tri-O-acetyl-d-glucal
  作者：Anna de Raadt、Arnold E. Stütz

  DOI：10.1016/0008-6215(91)80009-c

  日期：1991.11

  The reaction of protected glucuronic esters 2 and 7, as well as D-glucuronolactone derivative 11, with (trimethylsilyl)methylmagnesium chloride in ether led to the corresponding stable bis-silyl adducts 3, 8, and 12, respectively. In Peterson-type reactions catalysed with mild acid, these compounds yielded carbohydrate allylsilanes 4, 9, and 13, respectively. Synthons 4 and 9 were coupled with tri-O-acetyl-D-glucal

  受保护的葡糖醛酸酯2和7，以及D-葡糖醛酸内酯衍生物11与（三甲基甲硅烷基）甲基氯化镁在醚中的反应分别产生相应的稳定的双甲硅烷基加合物3、8和12。在用弱酸催化的彼得森型反应中，这些化合物分别生成碳水化合物烯丙基硅烷4、9和13。在三氟化硼催化的“碳-铁重排”反应中，合成子4和9与三-O-乙酰基-D-葡糖醛偶联，分别得到C连接的二糖，即所谓的“ C-二糖” 16和17 ，以合理的收益率。借助NMR在这些偶联产物的2,3-不饱和环的C-糖基碳上的异头构型的结构分配
• New Mechanistic Proposal for Some Heptamolybdate-Ion-Catalyzed Isomerizations
  作者：Branimir Klai?、Zlata Raza、Mauricio Sankovi?、Vitomir ?unji?

  DOI：10.1002/hlca.19870700107

  日期：1987.2.4

  d C(2) epimerization of D-glucose and racemization of D-glyceraldehyde proceed with comparable rates and activation parameters; HM catalyzes the isomerization of glucal and galactal triacetates as well. For all of the above transformations, a common, new mechanism is proposed that invokes stabilization of 3-oxa-allylic cation species by the central Mo(VI) atom.

  七钼酸根离子（HM）催化D-葡萄糖的C（2）差向异构化和D-甘油醛的外消旋化具有可比的速率和激活参数; HM还催化葡萄糖基和半乳糖基三乙酸酯的异构化。对于所有上述转换，提出了一种常见的新机制，该机制可以通过中心Mo（VI）原子激活3-氧杂-烯丙基阳离子物种的稳定性。