methyl 2,3,4-6-deoxy-α-D-manno-heptopyranoside | 40653-19-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-6-deoxy-α-D-manno-heptopyranoside
• 英文别名: methyl 6-deoxy-α-D-manno-heptopyranoside；Methyl-6-deoxy-α-D-mannoheptopyranosid
• CAS: 40653-19-8
• 化学式: C₈H₁₆O₆
• 分子量: 208.211
• InChiKey: HXRNNVCFNBIGQM-HEIBUPTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.18
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-6-deoxy-α-D-manno-heptopyranoside 在 吡啶 作用下， 反应 6.0h， 生成
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 16.08h， 生成 methyl 2,3,4-6-deoxy-α-D-manno-heptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297

文献信息

• Syntheses of methyl glycosides of 6-deoxyheptoses
  作者：Gerald O. Aspinall、Armando G. McDonald、Ramesh K. Sood

  DOI：10.1139/v94-037

  日期：1994.1.1

  by reduction of the resulting heptopyranosidurononitriles with diisobutylaluminum hydride, hydrolysis of the imine, further reduction with sodium borohydride, and catalytic O-debenzylation, give the corresponding methyl 6-deoxyheptopyranosides. Configurational change at C-4 of methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside to give the talo isomer was effected by oxidation followed

  已经制备了 6-脱氧-D-altro-heptose、6-deoxy-D-manno-heptose 和 6-deoxy-D-talo-heptose 的甲基 α-D-glycopyranosides。用氰化钾置换 2,3,4-三-O-苄基己基己基吡喃糖苷 6-三氟甲磺酸甲酯，然后用二异丁基氢化铝还原生成的吡喃基吡喃糖醛腈，水解亚胺，用硼氢化钠进一步还原，并催化 O-脱苄基，得到相应的甲基 6-脱氧庚基吡喃糖苷。甲基 6-脱氧-7-O-叔丁基二苯基甲硅烷基-α-D-甘露-吡喃庚糖苷在 C-4 处的构型变化以得到 talo 异构体是通过氧化和立体选择性还原来实现的。苷的1H核磁共振数据，