methyl 2,3-di-O-benzyl-α-D-glucopyranoside 4,6-cyclic sulfate | 124040-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-α-D-glucopyranoside 4,6-cyclic sulfate
• 英文别名: (4aR,6S,7R,8R,8aR)-6-methoxy-7,8-bis(phenylmethoxy)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3,2]dioxathiine 2,2-dioxide
• CAS: 124040-30-8
• 化学式: C₂₁H₂₄O₈S
• 分子量: 436.483
• InChiKey: HLEUTSBKAINTGU-ADAARDCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-glucopyranoside 4,6-cyclic sulfate 在 sodium azide 、 高氯酸 作用下， 生成 methyl 6-azido-2,3-di-O-benzyl-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Hydroxyamines as a New Motif for the Molecular Recognition of Phosphodiesters: Implications for Aminogloycoside–RNA Interactions

  摘要：

  DOI：

  10.1002/anie.199700951
• 作为产物：
  描述：

  (4aR,6S,7R,8R,8aR)-7,8-Bis-benzyloxy-6-methoxy-hexahydro-pyrano[3,2-d][1,3,2]dioxathiine 2-oxide 在 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 methyl 2,3-di-O-benzyl-α-D-glucopyranoside 4,6-cyclic sulfate
  参考文献：
  名称：

  Hydroxyamines as a New Motif for the Molecular Recognition of Phosphodiesters: Implications for Aminogloycoside–RNA Interactions

  摘要：

  DOI：

  10.1002/anie.199700951

文献信息

• Reactions on phenyl chlorosulfate at OH-1, -4, and -6 of aldohexopyranose derivatives. Formation of 1,2-oxazoline and 4,6-cyclic sulfate rings
  作者：Magdy M. Abdel-Malik、Arthur S. Perlin

  DOI：10.1016/0008-6215(89)84091-1

  日期：1989.6

  little or no interference with disaccharide synthesis at the nearby O-4 atom. Conformations of both cis - and trans -fused types of 4,6-cyclic sulfates are discussed. At an unsubstituted anomeric center, the course of reaction by phenyl chlorosulfate is determined by neighboring-group participation possibilities, and the strong leaving-group affinity of a phenylsulfate substituent. This is demonstrated

  摘要在苯基氯硫酸氢钠与不含OH-4和OH-6的化合物的反应中，例如在甲基2,3-二-O-苄基醛基吡喃吡喃糖苷中，伯羟基发生区域选择性取代，或者4，取决于实验条件，形成6-环硫酸盐。向二-O-苄基糖苷中添加6-（苯硫酸盐）取代基似乎几乎不干扰或几乎不干扰附近的O-4原子处的二糖合成。讨论了4，6-环硫酸盐的顺式和反式融合形式的构象。在未取代的异头异构中心，氯硫酸苯酯的反应过程取决于相邻基团的参与可能性以及苯硫酸酯取代基的强离去基团亲和力。2-乙酰氨基-4的60％转化证明了这一点，
• Applications of Cyclic Sulfates of <i>vic</i>-Diols:  Synthesis of Episulfides, Olefins, and Thio Sugars
  作者：Francisco G. Calvo-Flores、Pilar García-Mendoza、Fernando Hernández-Mateo、Joaquín Isac-García、Francisco Santoyo-González

  DOI：10.1021/jo962066b

  日期：1997.6.13

  A new efficient and expeditious one-pot synthesis of thiiranes and olefins from cyclic sulfates of vic-diols is described. Opening of cyclic sulfates with potassium thioacetate or potassium thiocyanate followed by treatment with sodium methoxide led to episulfides. Olefins were obtained when potassium selenocyanate was used as nucleophile, and the obtained monoesters were treated with sodium borohydride. This method was applied to acyclic polyols derived from chiral glycerine, 1,2-isopropylidenehexofuranoses with different subtituents at C-3, and dimethyl acetals derived from pentoses and hexoses. The methodology is highly versatile, and its applicability has been demonstrated by the synthesis of different 4- and 5-thiosugars by opening of the thiirane ring with sodium acetate or lithium aluminum hydride. Reduction with lithium aluminum hydride of the thiocyanate sulfate potassium salt obtained by the opening of cyclic sulfate with KSCN allowed the direct synthesis of 5-deoxy-4-thio- and 6-deoxy-5-thiosugars. Cyclic thiosugars with the sulfur atom in the ring are obtained by acidic hydrolysis of the 5-thiol derivatives of 1,2-O-isopropylidenehexofuranoses and 4-thiopentose dimethyl acetals. Using this method, an efficient synthesis of 5-thio-L-fucose as well as the synthesis of 2,5-dideoxy-4-thiofuranose is described.
• Synthesis of 6-Deoxyheptose Derivatives via Cyclic Sulfates and Oxetanes
  作者：Antonio Vargas-Berenguel、Francisco Santoyo-González、José A. Calvo-Asín、Francisco G. Calvo-Flores、Juan M. Expósito-López、Fernando Hernández-Mateo、Joaquín Isac-García、Juan J. Giménez Martínez

  DOI：10.1055/s-1998-2219

  日期：1998.12
• ABDEL-MALIK, MAGDY M.;PERLIN, ARTHUR S., CARBOHYDR. RES., 189,(1989) C. 123-133
  作者：ABDEL-MALIK, MAGDY M.、PERLIN, ARTHUR S.

  DOI：——

  日期：——