3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptose oxime | 263916-49-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptose oxime
• 英文别名: 2,3,4,6-tetra-O-acetyl-β-D-manopyranosylformaldoxime；tetra-O-acetyl-β-D-mannopyranosylformaldoxime；2,3,4,6-tetra-O-acetyl-β-D-mannopyranosylmethanal oxime
• CAS: 263916-49-0
• 化学式: C₁₅H₂₁NO₁₀
• 分子量: 375.332
• InChiKey: NCKZMAPJBSSLQZ-NJVJYBDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  147.02
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptose oxime 在 sodium hypochlorite 作用下， 以 二氯甲烷 、 水 为溶剂， 以75%的产率得到3,4-di(2,3,4,6-tetra-O-acetyl-β-D-manopyranosyl)-1,2,5-oxadiazole 2-oxide
  参考文献：
  名称：

  3,4-二吡喃糖基-1,2,5-恶二唑2-氧化物：合成与X射线结构

  摘要：

  3，4-二（2,3,4,6-四-O-乙酰基-β-d-甘露吡喃糖基）-1,2,5-恶二唑2-氧化物（7）是通过以下方法由d-甘露糖合成的作为关键步骤涉及甘露吡喃糖基一氧化氮2的二聚。三种方法用于生成一氧化氮：异氰酸酯介导的硝基甲基甘露糖衍生物4脱水，用盐酸水溶液处理醛肟5。次氯酸盐，和碱诱导的羟肟酰氯6的脱氯化氢作用。d-葡糖，d半乳糖，d-木糖和L- fucopyranosyl类似物8 - 11类似地制备。d-甘露糖衍生的1,2,5-恶二唑2-氧化物7的结构 通过X射线晶体学确定。

  DOI：

  10.1016/s0040-4020(02)01023-2
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-manopyranosyl(nitro)methane 在 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 苯 为溶剂， 以85%的产率得到3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-D-galacto-heptose oxime
  参考文献：
  名称：

  One-Step Conversion of C-Glycopyranosylnitromethanes to the Corresponding Methanal Oximes

  摘要：

  本文介绍了一种制备 C-吡喃糖基甲醛肟的新方法。用氢化三丁基锡和催化量的 1,1′-偶氮双（环己烷甲腈）处理δ-D-葡糖基、δ-D-甘露糖基、δ-D-半乳糖基、δ-D-氧代和δ-L-鼠李糖基构型的过 O-乙酰化 C-吡喃糖基硝基甲烷，可得到相应的甲醛肟，分离产率为 84-97%。

  DOI：

  10.1055/s-1998-1950

文献信息

• Generation and cycloaddition reactions of pyranose-1-carbonitrile oxides
  作者：Kenneth W.J Baker、Andrew Gibb、Andrew R March、R.Michael Paton

  DOI：10.1016/s0040-4039(01)00631-1

  日期：2001.6

  Stannate(II) reduction of the β-d-glucopyranosylnitromethane derivative 4 affords aldoxime 5, which provides access to the nitrile oxide 7, either on treatment with aq. hypochlorite, or via conversion to the hydroximoyl chloride 11 followed by base-mediated dehydrohalogenation. d-Galactose-, d-mannose- and d-xylose-derived nitrile oxides are generated similarly. The nitrile oxides either dimerise to

  β-d-吡喃葡萄糖基硝基甲烷衍生物4的Stannate（II）还原得到醛肟5，该醛肟在用NH 4 Cl水溶液处理时提供了与一氧化氮7的通道。次氯酸盐，或通过转化为羟肟基氯11，然后进行碱介导的脱卤化氢反应。d-半乳糖，d-甘露糖和d-木糖衍生的腈氧化物的生成方式相似。腈氧化物要么二聚为3,4-dipyranosyl-1,2,5- oxadiazole N-氧化物，要么在双极性亲和剂的存在下以环加成物形式被捕集。
• Precise Synthesis of Poly(macromonomer)s Containing Sugars by Repetitive ROMP and Their Attachments to Poly(ethylene glycol): Synthesis, TEM Analysis and Their Properties as Amphiphilic Block Fragments
  作者：James J. Murphy、Hirotoshi Furusho、R. Michael Paton、Kotohiro Nomura

  DOI：10.1002/chem.200700291

  日期：2007.11.5

  efficient placement of norbornene units on the side chain termini and their conversion into PMMs, facilitated by the Mo alkylidenes, proceeded in a living manner with the quantitative initiation. The methodology was applied to prepare poly(macromonomer)-graft-PEG [PEG: poly(ethylene glycol)], by the attachment of a pseudo phenol terminus on the PMM main chain to PEG-Ms(2) [MsO(CH(2)CH(2)O)(n)Ms, Ms=MeSO(2)]

  已通过重复开环易位聚合（ROMP）技术使用类型明确的钼引发剂[Mo（CHCMe（2）Ph）（NAr）（OR）（ 2）]，其中OR = OCMe（3），OCMeC（CF（3））（2）; Ar = 2,6-iPr（2）C（6）H（3），2,6-Me（2）C（6）H（3）。合成策略基于降冰片烯及其衍生物的聚合，提供带有糖（甘露糖，半乳糖，葡萄糖等）的二嵌段和三嵌段侧链，并通过O-（酯）和耐糖苷酶的C-（异恶唑啉）糖苷连接。在亚烷基钼的促进下，降冰片烯单元在侧链末端的有效放置及其向PMM的转化以定量引发的生动方式进行。将该方法应用于制备聚（大分子单体）-接枝-PEG [PEG：聚（乙二醇）]，通过在PMM主链上将假酚末端连接到PEG-Ms（2）[MsO（CH（2）CH（2）O）（n）Ms，Ms = MeSO（2）]，使用“ “ 方法。提示使用三氟乙酸/水（9：1）从各种超分子结构（包括PMMs，线
• Synthesis and structure of 2-pyransoylperimidines
  作者：Iain A.S. Smellie、Andreas Fromm、Stephen A. Moggach、R. Michael Paton

  DOI：10.1016/j.carres.2010.09.028

  日期：2011.1

  The first examples of 2-pyranosylperimidines are reported. The beta-D-glucopyranosyl nitrile oxide 5, generated by base-induced dehydrochlorination of the hydroximoyl chloride 4, reacted with 1,8-diaminonaphthalene to afford the 2-(beta-D-glucopyranosyl)perimidine 8. The D-xylo-, D-galacto-, D-manno- and D-glycero analogues 12, 15, 16 and 19 were prepared similarly. The glycals 9 and 13 were formed as by-products resulting from elimination of acetic acid from the corresponding pyranosylperimidines. The structure of D-glucose-derived perimidine 8 was established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.
• Behaviour of the Primary Nitro Group Under Denitration Conditions
  作者：Duy-Phong Pham-Huu、Mária Petrušová、James N. BeMiller、Ladislav Petruš

  DOI：10.1080/07328300008544067

  日期：2000.1

  Treatment of per-O-acetylated or acetalated glycosylnitromethanes derived from the common hexoses and pentoses with tributyltin hydride and a catalytic amount of a radical initiator [1,1'-azobis(cyclohexanecarbonitrile)] in refluxing benzene easily afforded the corresponding glycosylmethanal oximes in 84-97% yields. Per-O-acetylated C-beta-glycopyranosylmethanal oximes were employedfor synthesis of versatile C-beta-glycopyranosyl cyanides of the beta-D-gluco, beta-D-manno, beta-D-galacto, beta-D-xylo, and beta-L-rhamno configurations.