methyl 2,5-di-O-tosyl-β-D-glucofuranoside | 360773-17-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,5-di-O-tosyl-β-D-glucofuranoside
• 英文别名: Tos(-2)[Tos(-5)]b-Glcf1Me；[(2R,3R,4S,5S)-4-hydroxy-5-[(1R)-2-hydroxy-1-(4-methylphenyl)sulfonyloxyethyl]-2-methoxyoxolan-3-yl] 4-methylbenzenesulfonate
• CAS: 360773-17-7
• 化学式: C₂₁H₂₆O₁₀S₂
• 分子量: 502.563
• InChiKey: KUAHRTYWIZXUGG-FDKIHUSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 2,5-di-O-tosyl-β-D-glucofuranoside 在 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到methyl 2,3:5,6-dianhydro-β-D-mannofuranoside
  参考文献：
  名称：

  Sugar derivatives comprising oxiranes or alpha, beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides

  摘要：

  本发明涉及具有一般式（I）的杀虫化合物，它们的制备和应用于所述害虫或其生境，其中 表示C-C单键或双键; 表示-CH（R4）-，如果所述C-C是单键，则R4为氢，烷氧基或取代烷氧基，或R1，R4一起形成烷基二氧基或取代烷基二氧基基团; 或 表示═C（R5）-C（═O）-，如果所述C-C是双键，则R5为氢，卤素; R1，R2为氢，卤素，烷氧基，取代烷氧基或酯基，或R1，R2与它们所附着的碳原子一起表示环氧环; 或R1，R2一起表示烷基二氧基或取代烷基二氧基基团; R3表示-CH2R6（R6-酯基），氧杂环丙基或式中的基团，其中R7为氢或烷基，R8为苯基硫基，苯基硒基，苯基磺酸基或苯基亚砷酸基; R9为氢，乙氧羰基或氨基甲酰基。

  公开号：

  US20060025613A1
• 作为产物：
  描述：

  Methyl-2,5-di-O-tosyl-β-D-glucofuranosidurono-6,3-lacton 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以94%的产率得到methyl 2,5-di-O-tosyl-β-D-glucofuranoside
  参考文献：
  名称：

  有效合成与糖连接的α，β-不饱和γ-内酯

  摘要：

  已经制备了一系列结构多样的不饱和糖衍生的内酯。从环氧化物开始将α，β-丁烯内酯引入糖部分，而由羰基前体（醛，酮或内酯）构建α-亚甲基-γ-内酯。在最后一种情况下，开发了前所未有的Reformatsky型反应。

  DOI：

  10.1016/s0957-4166(01)00197-5

文献信息

• Sugar derivatives comprising oxiranes or alpha,beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides
  申请人：Instituto Politécnico de Santarém / Escola Superior Agraria

  公开号：EP1464649B1

  公开（公告）日：2010-10-20
• 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.
• Sugar derivatives comprising oxiranes or alpha, beta-unsaturated delta-lactones, process for their preparation and their utilisation as pesticides
  申请人：Justino Alberto Guerra Jorge

  公开号：US20080004339A1

  公开（公告）日：2008-01-03

  Pesticidal compounds of general formula (I) Wherein ----- represents a double bond; ----A— represents ═C(R 5 )—C(═O)—, wherein R represents hydrogen or halogen, R 1 and R 2 represent, independently, hydrogen, halogen, alkoxy, substituted alkoxy or an ester group; or R 1 and R 2 , together with the carbon atoms to which they are attached, represent an oxirane ring; or R 1 and R 2 , taken together, represent an alkylidenedioxy or substituted alkylidenedioxy group; and R 3 represents —CH 2 R 6 , wherein R 6 represents an ester group, oxiranyl, or a group of formula wherein R 7 represents hydrogen or alkyl, R 8 represents phenylsulfanyl, phenylselenyl, phenylsulfoxy or phenylselenoxy, and R 9 represents hydrogen, ethoxycarbonyl or carbamoyl and R 4 represents, independently, hydrogen, alkoxy or substituted alkoxy; and methods of making the compounds of formula (I) and methods for controlling pests wherein the pest dies as a result of contact with a compound of formula (I).
• Efficient synthesis of α,β-unsaturated γ-lactones linked to sugars
  作者：Amélia P. Rauter、José Figueiredo、Maria Ismael、Tana Canda、Josep Font、Marta Figueredo

  DOI：10.1016/s0957-4166(01)00197-5

  日期：2001.5

  A series of structurally diverse unsaturated sugar-derived lactones has been prepared. α,β-Butenolides were introduced to the sugar moiety starting from epoxides, while α-methylene-γ-lactones were constructed from a carbonyl precursor, either an aldehyde, a ketone or a lactone. In the last case, an unprecedented Reformatsky-type reaction has been developed.

  已经制备了一系列结构多样的不饱和糖衍生的内酯。从环氧化物开始将α，β-丁烯内酯引入糖部分，而由羰基前体（醛，酮或内酯）构建α-亚甲基-γ-内酯。在最后一种情况下，开发了前所未有的Reformatsky型反应。
• Sugar derivatives comprising oxiranes or alpha, beta-unsaturated gamma-lactones, process for their preparation and their utilisation as pesticides
  申请人：Justino Alberto Guerra Jorge

  公开号：US20060025613A1

  公开（公告）日：2006-02-02

  The present invention relates to pesticidal compounds with general formula (I), their preparation and application to said pests or their locus, wherein represents C—C single or double bond; represents —CH(R 4 )—, if said C—C is a single bond, R 4 hydrogen, alkoxy or substituted alkoxy, or R 1 , R 4 , taken together, form an alkylidenedioxy or substituted alkylidenedioxy group; or represents ═C(R 5 )—C(═O)—, if said C—C is a double bond, R 5 hydrogen, halogen; R 1 , R 2 -hydrogen, halogen, alkoxy, substituted alkoxy or ester group, or R 1 , R 2 , taken together with the carbon atoms to which they are attached, represent an oxirane ring; or R 1 , R 2 , taken together, represent an alkylidenedioxy or substituted alkylidenedioxy group; R 3 represents —CH 2 R 6 (R 6 -ester group), oxiranyl, or a group of formula wherein R 7 is hydrogen or alkyl, R 8 phenylsulfanyl, phenylselenyl, phenylsulfoxy or phenylselenoxy; and R 9 hydrogen, ethoxycarbonyl or carbamoyl.

  本发明涉及具有一般式（I）的杀虫化合物，它们的制备和应用于所述害虫或其生境，其中 表示C-C单键或双键; 表示-CH（R4）-，如果所述C-C是单键，则R4为氢，烷氧基或取代烷氧基，或R1，R4一起形成烷基二氧基或取代烷基二氧基基团; 或 表示═C（R5）-C（═O）-，如果所述C-C是双键，则R5为氢，卤素; R1，R2为氢，卤素，烷氧基，取代烷氧基或酯基，或R1，R2与它们所附着的碳原子一起表示环氧环; 或R1，R2一起表示烷基二氧基或取代烷基二氧基基团; R3表示-CH2R6（R6-酯基），氧杂环丙基或式中的基团，其中R7为氢或烷基，R8为苯基硫基，苯基硒基，苯基磺酸基或苯基亚砷酸基; R9为氢，乙氧羰基或氨基甲酰基。