6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose | 121195-24-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (3aR,5R,6S,6aR)-5-[(1R)-2-azido-1-phenylmethoxyethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 121195-24-2
• 化学式: C₂₃H₂₇N₃O₅
• 分子量: 425.484
• InChiKey: CGKKLCAOMMBMCN-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  60.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 在 三苯基膦 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 16.17h， 以48%的产率得到3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose
  参考文献：
  名称：

  Stereocontrolled Transformation of Nitrohexofuranoses into Cyclopentylamines via 2-Oxabicyclo[2.2.1]heptanes:  Incorporation of Polyhydroxylated Carbocyclic β-Amino Acids into Peptides

  摘要：

  graphicA promising new strategy for the transformation of nitrohexofuranoses into cyclopentylamines, based on intramolecular cyclization followed by controlled opening of the resulting 2-oxabicyclo[2.2.1]heptane derivatives, allowed the first total synthesis of a carbocyclic beta-amino acid and its incorporation into peptides. This strategy also afforded a new route to cyclopentylamines with well-known glycosidase inhibition properties.

  DOI：

  10.1021/ol034127f
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 sodium azide 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 45.0h， 生成 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  由D-葡萄糖实际合成脱氧甘露霉素和（2s，3R，4R，5R）-3,4,5-三羟基哌酸

  摘要：

  脱氧甘露糖霉素[1,5-二脱氧-1,5-亚氨基-D-甘露糖醇]可以由二丙酮葡萄糖经十步以中等量制备，总收率为35％。关键步骤是无论糖的端基构型如何，都通过C-6处的氮官能团通过甲基葡糖呋喃糖苷的C-2处三氟甲磺酸酯的分子内亲核取代形成哌啶环。报道了（2S，3R，4R，5R）-3，4，5-三羟基哌酸的合成。

  DOI：

  10.1016/0040-4020(89)80060-2

文献信息

• Metal-Free Route to Carboxylated 1,4-Disubstituted 1,2,3-Triazoles from Methoxycarbonyl-Modified Vinyl Sulfone
  作者：Jayanta Das、Santu Dey、Tanmaya Pathak

  DOI：10.1021/acs.joc.9b02443

  日期：2019.12.6

  A metal-free alternative to the regioselective synthesis of carboxylated 1,4-disubstituted 1,2,3-triazoles (1,4-cDTs) has been accomplished. A methoxycarbonyl-substituted vinyl sulfone on reactions with organic azides resulted in the formation of 1,4-cDTs in an operationally simple route. The reaction, carried out with a variety of organic azides containing free alcohol, acid, Boc-protected amine,

  现已实现了无金属替代方案，可选择性取代羧基化的1,4-二取代1,2,3-三唑（1,4-cDTs）。与有机叠氮化物反应时，甲氧基羰基取代的乙烯基砜导致以操作简单的方式形成1,4-cDTs。发现该反应是使用多种有机叠氮化物进行的，这些有机叠氮化物具有普遍性质，该有机叠氮化物包含游离醇，酸，Boc保护的胺，酯，保护糖，长链烷烃，苄基，9-甲基蒽基和胆固醇基，提供了许多新的化学实体；叠氮化物的反应主要生成所需的产物和一些未预期的产物。本文首次报道了任何1,4-二取代1,2的有针对性的无金属合成，
• Synthesis of tetrazole fused azepanes and quantum chemical topology study on the mechanism of the intramolecular cycloaddition reaction
  作者：M. S. Pino-Gonzalez、A. Romero-Carrasco、S. Calvo-Losada、N. Oña-Bernal、J. J. Quirante、F. Sarabia

  DOI：10.1039/c7ra10899k

  日期：——

  The synthesis of novel tetrazolo azepanes from azido nitriles by 1,3 intramolecular dipolar cycloaddition starting from monosaccharide derivatives is described. A quantum chemical topological study on the intramolecular cyclization process has been conducted rendering a pseudo-concerted mechanism. Conformational study was done for the final products which showed a preferential twist boat conformation

  描述了由叠氮腈通过从单糖衍生物开始的1,3分子内偶极环加成反应来合成新型四唑叠氮烷。已经进行了分子内环化过程的量子化学拓扑研究，从而提供了一种伪令人信服的机理。对最终产物进行了构象研究，该产物显示出优先的扭曲船构象，理论上适用于甘露糖苷酶抑制作用。但是，四唑类对糖苷酶没有明显的抑制作用。
• FLEET, GEORGE W. J.;RAMSDEN, NIGEL G.;WITTY, DAVID R., TETRAHEDRON., 45,(1989) N 1, C. 327-336
  作者：FLEET, GEORGE W. J.、RAMSDEN, NIGEL G.、WITTY, DAVID R.

  DOI：——

  日期：——
• [EN] MONOSACCHARIDE DERIVATIVES<br/>[FR] DERIVES DE MONOSACCHARIDE
  申请人：RANBAXY LAB LTD

  公开号：WO2005092907A2

  公开（公告）日：2005-10-06

  The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases such as bronchial asthma, rheumatoid arthritis, type I diabetes, multiple sclerosis, allograft rejection or psoriasis. Pharmacological compositions containing compounds disclosed herein and the methods of treating bronchial asthma, chronic obstructive pulmonary disease, rheumatoid arthritis, multiple sclerosis, type I diabetes, psoriasis, allograft rejection, and other inflammatory and/or autoimmune disorders, using the compounds are also provided.
• A practical synthesis of deoxymannojirimycin and of (2s,3R,4R,5R)-3,4,5-trihydroxypipecolic acid from D-glucose
  作者：George W.J. Fleet、Nigel G. Ramsden、David R Witty

  DOI：10.1016/0040-4020(89)80060-2

  日期：1989.1

  Deoxymannojirimycin [1,5-dideoxy-1,5-imino-D-mannitol] may be prepared in moderate amounts in an overall yield of 35% in ten steps from diacetone glucose; the key step is formation of the piperidine ring by intramolecular nucleophilic displacement of a triflate at C-2 of a methyl glucofuranoside by a nitrogen function at C-6, irrespective of the anomeric configuration of the sugar. A synthesis of (2S

  脱氧甘露糖霉素[1,5-二脱氧-1,5-亚氨基-D-甘露糖醇]可以由二丙酮葡萄糖经十步以中等量制备，总收率为35％。关键步骤是无论糖的端基构型如何，都通过C-6处的氮官能团通过甲基葡糖呋喃糖苷的C-2处三氟甲磺酸酯的分子内亲核取代形成哌啶环。报道了（2S，3R，4R，5R）-3，4，5-三羟基哌酸的合成。