5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose | 108788-44-9

• 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: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose
• 英文别名: 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose；[(2R,3R)-3-[(3aR,5S,6S,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]oxiran-2-yl]methanol
• CAS: 108788-44-9
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: DKUVAQMARKFXRP-BKQXGZDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose 在 sodium azide 、 硼酸三甲酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以92%的产率得到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
• 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 、 silica gel 、 红铝 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 1.66h， 生成 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose
  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 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。
• 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.