methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside | 23339-17-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside
• 英文别名: methyl 2,3-dideoxy-4,6-di-O-acetyl-D-glucopyranoside；[(2R,3S)-3-acetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 23339-17-5
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: XHUMGZABGNVWGH-MTULOOOASA-N

物化性质

• 沸点：
  314.2±42.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside 在 三甲基氯硅烷 、 氨 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 28.5h， 生成 1-(2',3'-Dideoxy-β-D-glucopyranosyl)uracil
  参考文献：
  名称：

  Warum Pentose- and nichtHexose-Nucleinsäuren??。泰尔二世。寡核苷酸aus 2'，3'-Dideoxy-β-D-glucopyranosyl-Bausteinen（'Homo-DNS'）：Herstellung。†

  摘要：

  为什么是戊糖而不是己糖核酸？第二部分。包含2'，3'-双脱氧-β-D-吡喃葡萄糖基结构单元的寡核苷酸的制备（7）

  DOI：

  10.1002/hlca.19920750503
• 作为产物：
  描述：

  乙酰化葡萄烯糖 在 palladium on activated charcoal montmorillonite K-10 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hexopyranoside
  参考文献：
  名称：

  Brevetoxin-B 的全合成

  摘要：

  Brevetoxin-B (BTX-B) 由赤潮生物 Gymnodium breve Davis 产生，是第一个在结构上被阐明的海洋多环醚成员，也是最有效的神经毒素之一。结构特征是具有23个立体中心的反式稠合多环醚环系统。其独特、复杂的结构和强大的生物活性引起了合成有机化学家的关注。BTX-B 的全合成是通过 ABCDEFG 和 IJK 环段的偶联完成的，其中每个醚环都是在 SmI2 诱导的分子内环化、羟基环氧化物的 6-内环化的基础上立体选择性和有效地构建的，闭环烯烃复分解和 SmI2 诱导的分子内 Reformatsky 型反应。

  DOI：

  10.1021/ja0449269

文献信息

• Synthesis of (4s,5r)-(+)-factor, a proposed autoregulator of anthracycline biosynthesis
  作者：Leonidas Stamatatos、Pierre Sinay、Jean-René Pougny

  DOI：10.1016/s0040-4020(01)91120-2

  日期：1984.1

  A 12 steps synthesis of the 6-C-(n-butyl)-2,3,6-trideoxy-D-erythro-1, 4-lactone 14 from commercial 2,3,6-tri-O-acetyl-D-glucal is described.

  由商业2,3,6-三-O-乙酰基-D-进行12步合成6-C-（正丁基）-2,3,6-三苯氧基-D-赤藓醇-1，4-内酯14描述了葡萄糖。
• Model studies directed towards microalgal polyether toxins. Use of 2-phenyl-sulphonyl cyclic ethers in the preparation of trans, syn, trans α-alkyl, β-hydroxy-substituted tetrahydropyran subunits
  作者：Eleuterio Alvarez、Milagros Rico、Rosa M. Rodriguez、Dácil Zurita、Julio D. Martin

  DOI：10.1016/s0040-4039(00)92095-1

  日期：1992.6

  A synthesis of optically active C7- and C8 -tetrahydropyranyl subunits with suitable functionalities for futher elaboration of transfused polyether toxins was achieved from glucal acetate via the use of 2-phynylsulphonyl intermediates. The bicyclic trans,syn,trans oxane-oxepanyl substructure 26 was prepared through the application of this methodology.

  通过使用2-邻苯二甲酰基磺酰基中间体，从乙酸葡糖醛中合成了具有合适官能度的光学活性C 7-和C 8-四氢吡喃基亚基，用于进一步加工输注的聚醚毒素。通过应用该方法制备了双环反式，顺式，反式，氧杂环戊烷-氧杂戊基亚结构26。
• Chiral synthesis of the CD ring unit of paclitaxel from d-glucal
  作者：Takayuki Momose、Masaki Setoguchi、Toshiki Fujita、Hitoshi Tamura、Noritaka Chida

  DOI：10.1039/b006170k

  日期：——

  The chiral synthesis of the fully functionalized CD ring unit of paclitaxel 3 is described; the three component coupling reaction of a cyclohexenone derived from D-glucal by way of Ferrier’s carbocyclization with vinyl cuprate and formaldehyde effectively constructed the carbon framework of 3.

  描述了紫杉醇3的全功能化CD环单元的手性合成；由D-葡糖醛衍生的环己烯酮通过Ferrier碳环化与乙烯基铜酸盐和甲醛的三组分偶联反应有效地构建了3的碳骨架。
• Towards a Synthesis of Vigabatrin Using Glycal Chemistry
  作者：S. Boga、J. Aidhen、I. Aidhen

  DOI：10.3390/10080871

  日期：——

  Application of the Ferrier rearrangement led to a novel carbohydrate based synthetic route to 4-aminohexenoic acid viz. (R) and (S)-vigabatrin. The potential of D- glucose or D-galactose as the chiral starting materials for the synthesis of (R) and (S)- vigabatrin has been explored.

  费里尔重排的应用为4-氨基己烯酸（即（R）和（S）-维加巴林）开辟了一条全新的碳水化合物合成途径。D-葡萄糖或D-半乳糖作为（R）和（S）-维加巴林合成的手性起始原料的潜力已经得到探索。
• Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations
  作者：Eleuterio Alvarez、Maria T. Diaz、Ricardo Perez、Jose L. Ravelo、Alicia Regueiro、Jose A. Vera、Dacil Zurita、Julio D. Martin

  DOI：10.1021/jo00089a034

  日期：1994.5

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.