6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose | 108788-52-9

• 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-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
• 英文别名: 6-azide-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose；6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-D-glycero-α-D-gluco-heptofuranose；(1R,2R)-1-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-azidopropane-1,3-diol
• CAS: 108788-52-9
• 化学式: C₁₇H₂₃N₃O₆
• 分子量: 365.386
• InChiKey: YIZQLCAQHCZIJS-YTQIUSBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose 在 palladium 10% on activated carbon 、 甲酸铵 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 26.0h， 生成 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
  参考文献：
  名称：

  Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

  摘要：

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.005
• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 sodium tetrahydroborate 、 sodium periodate 、 sodium azide 、 硼酸三甲酯 、 silica gel 、 红铝 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 49.66h， 生成 6-azido-3-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
  参考文献：
  名称：

  Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

  摘要：

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.005

文献信息

• 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。
• Synthesis of a new amino acid-antibiotic, oxetin and its three stereoisomers.
  作者：YUTAKA KAWAHATA、SUGURU TAKATSUTO、NOBUO IKEKAWA、MASATSUNE MURATA、SATOSHI OMURA

  DOI：10.1248/cpb.34.3102

  日期：——

  Oxetin (1a), a unique antibiotic having an oxetane ring, and its three stereoisomers (1b, 1c, and 1d) were synthesized from the known aldehyde (6) by utilizing a highly regio- and stereoselective epoxide ring-opening reaction. The biological activities of these oxetin stereoisomers were compared.

  Oxetin（1a）是一种独特的含氧杂环的抗生素，其三种立体异构体（1b、1c和1d）是通过利用高度区域和立体选择性环氧化开环反应从已知的醛（6）合成的。对这些氧杂环立体异构体的生物活性进行了比较。
• Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide
  作者：Vrushali H. Jadhav、Omprakash P. Bande、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tetasy.2010.01.007

  日期：2010.2

  The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.
• Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes
  作者：Noe Oña、Antonio Romero-Carrasco、M. Soledad Pino-González

  DOI：10.1016/j.tetasy.2012.12.005

  日期：2013.2

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.