2,5-anhydro-1-deoxy-3,4:6,7-di-O-isopropylidene-D-mannohept-1-enitol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-1-deoxy-3,4:6,7-di-O-isopropylidene-D-mannohept-1-enitol
• 英文别名: (3aS,6R,6aS)-6-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-4-methylidene-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole
• 化学式: C₁₃H₂₀O₅
• 分子量: 256.299
• InChiKey: XBOXCKJXBXIQBJ-NCYANSMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-1-deoxy-3,4:6,7-di-O-isopropylidene-D-mannohept-1-enitol 在 potassium osmate(VI) dihydrate 、 水 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 36.0h， 生成 D-Mannoheptulose
  参考文献：
  名称：

  Highly Efficient Synthesis of Ketoheptoses

  摘要：

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

  DOI：

  10.1021/ol2012764
• 作为产物：
  描述：

  D-甘露糖 在 硫酸 、 乙酸酐 、 二甲基亚砜 作用下， 以 甲苯 为溶剂， 反应 38.0h， 生成 2,5-anhydro-1-deoxy-3,4:6,7-di-O-isopropylidene-D-mannohept-1-enitol
  参考文献：
  名称：

  Highly Efficient Synthesis of Ketoheptoses

  摘要：

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.

  DOI：

  10.1021/ol2012764

文献信息

• Glyconothio-<i>O</i>-lactones. Part III. Thermolysis of a 4,5-Dihydro-1,2,3- and a 2,5-Dihydro-1,3,4-thiadiazole
  作者：Bruno Bernet、Thomas Mäder、Andrea Vasella

  DOI：10.1002/hlca.19970800422

  日期：1997.6.30

  HPLC of the thermolysis product of 2 gave the enethiol 17, the sulfide 19, and the mercapto alcohol 18 as secondary products. Thermolysis of the thiirane 9 at 110–120° (Scheme 4) led to the anomeric thiirane 12 which was transformed into mixtures of the enethiol 17 and the enol ether 7. Addition of H2O to 17 and 7 gave the corresponding hemiacetals 18 and 20. The mechanism of the thermolysis of the dihydrothiadiazoles

  将CH 2 N 2加到2,3：5,6-二-O-异亚丙基-1-硫代甘露糖醇-1,4-内酯（1）中，得到2,5-二氢-1,3,4-噻二唑2和4,5-二氢-1,2,3-噻二唑3。第一阶观察动力学的热解3（方案3）在80-110°用C 6 d 5 Cl溶液和第2（方案3中CDC1）在20-35° 3，分别。1,2,3-噻二唑3导致了硫杂丙环的混合物9中，起始thionolactone 1中，硫羰-1,5-内酯8和烯醇醚7，而异构体1,3,4-噻二唑2则生成异头噻烷9和12的混合物，O氢S，O，O-邻内酯α-D- 14，S-甲基硫酯15，S，S，O-正内酯13和2,3：5,6-二-O异亚丙基-甘露糖-1,4-内酯（16）。通过半制备超临界流体色谱（SFC）分离出热分解的纯产物，而制备HPLC则导致部分或完全分解。因此，通过制备型HPLC分离了3的粗产物，在115–120°下被未知S物质污染的β-D-
• Heck-type cross-coupling between halo-exo-glycals and endo-glycals: a practical way to achieve C-glycosidic disaccharides
  作者：Yongfeng Tao、Ning Ding、Sumei Ren、Yingxia Li

  DOI：10.1016/j.tetlet.2013.08.118

  日期：2013.11

  An effective Heck-type cross-coupling reaction between halo-exo-glycals and endo-glycals to achieve C-glycosidic disaccharides has been developed. Using Pd(OAc)(2) as the catalyst, dppp as ligand and K2CO3 as base, the reactions gave C-glycosidic products in good to excellent yields with exclusive stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.
• Highly Efficient Synthesis of Ketoheptoses
  作者：Daniel Waschke、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol2012764

  日期：2011.7.15

  A reliable, facile, high overall yielding and diastereoselective synthesis of ketoheptoses was developed and applied for preparation of the two most diabetogenic ketoheptoses as well as in a modified version for the synthesis of kamusol.