methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside | 68396-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside
• 英文别名: Methyl 6-amino-6-deoxy-β-D-glucopyranoside；methyl 6-deoxy-6-amino-β-D-glucopyranoside；methyl 6-amino-6-deoxy-α-L-idopyranoside；(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-methoxyoxane-3,4,5-triol
• CAS: 68396-86-1
• 化学式: C₇H₁₅NO₅
• 分子量: 193.2
• InChiKey: BJYPUAVFYCRNFH-XUUWZHRGSA-N

物化性质

• 沸点：
  369.5±42.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  105
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside 在 三乙胺 、 calcium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.5h， 生成 (5R)-(4-Deoxy-1-O-methyl-β-D-xylopyranoso)<5,4-e>tetrahydro-1,3-oxazine-2-thione
  参考文献：
  名称：

  Chiral 2-thioxotetrahydro-1,3-O,N-heterocycles from carbohydrates. 2. Stereocontrolled synthesis of oxazolidine pseudo-C-nucleosides and bicyclic oxazine-2-thiones

  摘要：

  DOI：

  10.1021/jo00071a032
• 作为产物：
  描述：

  甲基 Β-D-吡喃葡萄糖苷 在 palladium on activated charcoal 叠氮化锂 、 四溴化碳 、 氢气 、 三苯基膦 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 methyl 6-deoxy-6-tert-butoxycarbonylamino-β-D-glucopyranoside
  参考文献：
  名称：

  葡萄糖-苯丁酸氮芥衍生物的合成及其通过人GLUT1葡萄糖转运蛋白的识别。

  摘要：

  对脑内肿瘤使用化学治疗剂的局限性在于它们对中枢神经系统的吸收不良。增强大脑输送能力的一种方法是设计通过血脑屏障的饱和营养载体之一，高效的大脑和红细胞葡萄糖转运蛋白同工型GLUT1输送到大脑中的药物。由于血脑屏障的GLUT1己糖转运蛋白也存在于红细胞上，因此设计用于由GLUT1转运蛋白转运的新化合物已在人红细胞上进行了研究，它们代表了独特的，易于获得的人GLUT1表达细胞。在本文中，我们描述了四种葡萄糖-苯丁酸氮芥衍生物的合成，即甲基6-O-4 [双（2-氯乙基）氨基]苯丁酸酯和酰基-β-D-吡喃葡萄糖苷（3），6-O-4- [双（2-氯乙基）氨基]苯磺酰基-D-吡喃葡萄糖（6），甲基6- [4- [双（2-氯乙基）氨基]苯丁酰基an] -6-脱氧-β- D-吡喃葡萄糖苷（9）和6- [4- [双（2-氯乙基）氨基]苯丁酰氨基酰胺基] -6-脱氧-D-吡喃葡萄糖（10），以及它们与人类GLU

  DOI：

  10.1016/s0014-2999(96)00796-0

文献信息

• Synthesis of 6-Amino-6-deoxy-L-idopyranosides
  作者：Keiji Matsuda、Tsutomu Tsuchiya、Takahiro Torii、Sumio Umezawa

  DOI：10.1246/bcsj.59.1397

  日期：1986.5

  Methyl 6-amino-6-deoxy-α- and -β-l-idopyranosides have been prepared from 3-O-acetyl-1,2-O-isopropylidene-d-glucofuranose via 5,6-anhydro-1,2-O-isopropylidene-l-idofuranose and the azide product derived from it. Isopropyl 6-amino-6-deoxy-α- and -β-l-idopyranosides were prepared from 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-l-idopyranosyl chloride and 2-propanol. Nonprotected α- and β-l-idopyranosides were distinguished by their J1,2 proton couplings.

  甲基6-氨基-6-脱氧-α-和-β-l-呋喃糖苷是通过5,6-脱水-1,2-O-异丙基氟糖和从中衍生的叠氮化物产品，从3-O-乙酰-1,2-O-异丙基氟糖制备的。异丙基6-氨基-6-脱氧-α-和-β-l-呋喃糖苷是通过6-叠氮-2,3,4-三-O-苄基-6-脱氧-α-l-呋喃糖苷氯化物和2-丙醇制备的。非保护的α-和β-l-呋喃糖苷通过它们的J1,2质子耦合进行了区分。
• Quantifying the Electronic Effects of Carbohydrate Hydroxy Groups by Using Aminosugar Models
  作者：Christian M. Pedersen、Jacob Olsen、Azra B. Brka、Mikael Bols

  DOI：10.1002/chem.201100020

  日期：2011.6.14

  their pKa values determined by titration. These model compounds were chosen because they are the amino derivatives of the most common glycosyl acceptors. From this study it was possible to evaluate the electron density at each of the given positions in the carbohydrate and compare them. Some general trends were observed: The basicity of the amino groups decreases in the order 6‐NH2>3‐NH2>2‐NH2>4‐NH2

  合成了具有α-和β-葡萄糖，α-半乳糖或α-甘露糖立体化学的甲基氨基脱氧糖苷，在四个可能的非异头位置中均具有氨基官能团，并通过滴定确定了其p K a值。选择这些模型化合物是因为它们是最常见的糖基受体的氨基衍生物。通过这项研究，有可能评估碳水化合物中每个给定位置的电子密度并进行比较。观察到一些一般趋势：氨基的碱度以6-NH 2 > 3-NH 2 > 2-NH 2 > 4-NH 2的顺序降低。（指的是位置）。当糖环上的一个或多个取代基为轴向时，氨基脱氧糖α的碱性通常会增加。当胺对氧原子为反平面时，碱度降低。这些发现与从糖基化化学和糖的区域选择性保护获得的观察结果一致。
• Process for producing glucopyranose-nitrosourea compounds and novel
  申请人：Tokyo Tanabe Company, Limited

  公开号：US04156777A1

  公开（公告）日：1979-05-29

  Glucopyranose-nitrosourea compounds having lower alkyl group and/or 2-chloroethyl group as substituent(s), are produced at high yield by reacting amino-glucopyranose compounds having lower alkoxy group and/or amino group(s) (or an acid-added amino group) as substituent(s), with o-nitro- or o-cyano-phenyl N-substituted-N-nitrosocarbamate compounds having lower alkyl group or 2-chloroethyl group as substituent. 1-(Lower alkyl or 2-chloroethyl)-3-(D-glucopyranos-6-yl)-1-nitrosourea compounds included within the scope of the nitrosourea compounds are novel. The nitrosourea compounds produced by this invention all show antitumor activity, among which the novel compounds exhibit excellent physical and pharmacological properties.

  葡萄糖吡喃糖基-硝基脲化合物具有较低的烷基基团和/或2-氯乙基基团作为取代基，在高产率下通过将具有较低烷氧基和/或氨基（或加酸氨基）作为取代基的氨基葡萄糖吡喃糖化合物与具有较低烷基基团或2-氯乙基基团作为取代基的o-硝基或o-氰基苯基N-取代-N-亚硝基氨基甲酸酯化合物反应而产生。包含在硝基脲化合物范围内的1-(较低烷基或2-氯乙基)-3-(D-葡萄糖吡喃糖基-6-基)-1-硝基脲化合物是新颖的。本发明产生的硝基脲化合物均显示抗肿瘤活性，其中新颖化合物展现出优异的物理和药理特性。
• Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds
  作者：Paul V Murphy、Julie L O'Brien、Lorraine J Gorey-Feret、Amos B Smith

  DOI：10.1016/s0040-4020(03)00208-4

  日期：2003.3

  The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-aniino-beta-D-glucopyranoside and 6-deoxy-6-amino- beta-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Cytotoxic ceramides and glycerides from the roots of Livistona chinensis
  作者：Xiaobin Zeng、Limin Xiang、Chen-Yang Li、Yihai Wang、Guofu Qiu、Zhen-xue Zhang、Xiangjiu He

  DOI：10.1016/j.fitote.2012.01.008

  日期：2012.4

  A 70% ethanol extract of the roots of Livistona chinensis has been investigated, led to the isolation of 13 compounds, including a new ceramide, (2S,35,4R,9Z)-2-[(2R)-2-hydroxytricosanoylamino]-9-octadecene-1,3,4-triol (2), a new glycosyl ceramide, 1-O-beta-D-glucopyranosyl-(2S,3S,4R,9Z)-2-[(2R)-2-hydroxydocosanoylamino]-9-octadecene-1,3,4-triol (3), three new monoacylglycerols, 1-(34-hydroxytetratriacontanoyl)-sn-glycerol (9), 1-[nonadeca-(9Z,12Z)-dienoyl]-sn-glycerol (10), and 1-[12-hydroxypentatriaconta-(13E,15Z)-dienoyl]-sn-glycerol (11), a new diacylglycerol, 1-(heptadeca-6Z,9Z-dienoyl)-3-(octadeca-6Z,9Z,12Z-trienoyl)-sn-glycerol (12), as well as a new diacylglycerol aminoglycoside, 1-octadecanoyl-2-nonadecanoyl-3-O-(6-amino-6-deoxy)-beta-D-glucopyranosyl-sn-glycerol (13). The structures of new compounds were elucidated. based on spectroscopic, zymologic and chemical methods. Among the compounds tested, compounds 3, 4 and 13 showed significantly antiproliferative effects against the human tumor cell lines (K562, HL-60, HepG2, and CNE-1) with the IC50 of 10-65 mu M. To our knowledge, this is first report of the occurrence of ceramides and acylglycerols in the genus Livistona. (C) 2012 Elsevier B.V. All rights reserved.