methyl 2,3-anhydro-5,6-di-O-benzyl-α-D-allofuranoside | 791111-18-7

• 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: methyl 2,3-anhydro-5,6-di-O-benzyl-α-D-allofuranoside
• 英文别名: (1R,2R,4S,5R)-2-[(1R)-1,2-bis(phenylmethoxy)ethyl]-4-methoxy-3,6-dioxabicyclo[3.1.0]hexane
• CAS: 791111-18-7
• 化学式: C₂₁H₂₄O₅
• 分子量: 356.419
• InChiKey: XNVHHDUUTDJIIJ-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-甲苯硫酚 、 methyl 2,3-anhydro-5,6-di-O-benzyl-α-D-allofuranoside 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-(1,2-dibenzyloxyethyl)-5-methoxy-4-[(4-methylphenyl)sulfanyl]tetrahydrofuran-3-ol
  参考文献：
  名称：

  从非环状乙烯基砜改性的碳水化合物到在所有三个环碳原子上官能化的环丙烷的非对映选择性独特路线†

  摘要：

  与当前使用金属催化途径进行环丙烷化的趋势背道而驰，具有末端双键和适当位置的离去基团的戊糖基和己糖基乙烯基砜改性的碳水化合物与一系列亲核试剂以立体选择性方式反应，生成无数种在全部三个环碳原子上取代的环丙烷的数目。

  DOI：

  10.1021/jo802709q
• 作为产物：
  描述：

  methyl 5,6-di-O-benzyl-3-O-tosyl-α,β-D-glucofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以65%的产率得到methyl 2,3-anhydro-5,6-di-O-benzyl-β-D-allofuranoside
  参考文献：
  名称：

  Synthesis of Phenylseleno Sugars from Epoxides and of α,β‐Unsaturated Carbonyl Derivatives for the Study of Their Insecticidal Activity

  摘要：

  This work reports the synthesis of sugar epoxides and their derivatives obtained by reaction with the dianion of phenyl selenoacetic acid. Approaches to the introduction of alpha,beta-unsaturated carbonyl units in pyranoid systems were investigated. Preparation of a protected D-glycero-hex-3-enepyranosid-2-ulose and of a D-erythro-hex-2-enono-1,5-lactone is described. Some of the synthesized compounds possess insecticidal activity against fruit flies, house flies, and white flies.

  DOI：

  10.1081/car-200030077

文献信息

• A Diastereoselective Unique Route to Cyclopropanes Functionalized at All Three Ring Carbon Atoms from Acyclic Vinyl Sulfone-Modified Carbohydrates
  作者：Ananta Kumar Atta、Tanmaya Pathak

  DOI：10.1021/jo802709q

  日期：2009.4.3

  In a departure from the current trend of using metal-catalyzed routes to cyclopropanation, pentosyl and hexosyl vinyl sulfone-modified carbohydrates having the terminal double bond and a suitably positioned leaving group are reacted in a stereoselective fashion with a series of nucleophiles to yield a myriad of cyclopropanes substituted at all three ring carbon atoms.

  与当前使用金属催化途径进行环丙烷化的趋势背道而驰，具有末端双键和适当位置的离去基团的戊糖基和己糖基乙烯基砜改性的碳水化合物与一系列亲核试剂以立体选择性方式反应，生成无数种在全部三个环碳原子上取代的环丙烷的数目。
• Synthesis of Phenylseleno Sugars from Epoxides and of α,β‐Unsaturated Carbonyl Derivatives for the Study of Their Insecticidal Activity
  作者：Amélia P. Rauter、Tana Canda、Jorge Justino、Maria I. Ismael、José A. Figueiredo

  DOI：10.1081/car-200030077

  日期：2004.12.29

  This work reports the synthesis of sugar epoxides and their derivatives obtained by reaction with the dianion of phenyl selenoacetic acid. Approaches to the introduction of alpha,beta-unsaturated carbonyl units in pyranoid systems were investigated. Preparation of a protected D-glycero-hex-3-enepyranosid-2-ulose and of a D-erythro-hex-2-enono-1,5-lactone is described. Some of the synthesized compounds possess insecticidal activity against fruit flies, house flies, and white flies.