2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-diethoxyphophinoyl-D-mannitol | 102292-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-diethoxyphophinoyl-D-mannitol
• 英文别名: (2S,3S,4R,5R)-2-(diethoxyphosphorylmethyl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 102292-67-1
• 化学式: C₃₁H₃₉O₇P
• 分子量: 554.62
• InChiKey: ZKWAVJYCDUVCMR-OMRVPHBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-diethoxyphophinoyl-D-mannitol 在 甲醇 、 硫酸 、 sodium 作用下， 生成 ((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp): a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp)

  摘要：

  The stereospecific synthesis of 5-phospho-alpha -D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00118-6
• 作为产物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 二甲基硫 、 四丁基氟化铵 、 臭氧 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-diethoxyphophinoyl-D-mannitol
  参考文献：
  名称：

  C-阿拉伯呋喃糖基化合物的合成。d-阿拉伯糖1,5-双磷酸酯的膦酸酯和羧酸酯等排体

  摘要：

  摘要用N-溴代琥珀酰亚胺对3,4,6-tri-O-苄基-1,2-二脱氧-d-阿拉伯糖-hex-1-烯醇进行亲电介导的环化反应主要产生2,5-脱水-3,4,6 -三-O-苄基-1-溴-1-脱氧-d-葡萄糖醇（10）。在成功合成β-d-阿拉伯糖1,5-双磷酸酯（1）的膦酸酯类似物（即2,5-脱水-1-脱氧1-膦酰基-d-）的成功合成中，这一显然由动力学控制的反应至关重要。具有高立体选择性的6-磷酸葡萄糖醇（4）。相反，将亚甲基二膦酸四乙酯的钠盐与2,3,5-三-O-苄基-d-阿拉伯糖（7）缩合，得到的膦酸酯化合物稍微富含2,5-脱水-d-甘露糖醇（α）。异构体。在稳定的phosphor烷与7的维蒂希-迈克尔反应中，α异构体占优势。由于甲基3,6-脱水-4,5的平衡，7-三-O-苄基-2-脱氧-d-甘油-d-半乳糖-（33）和-d-gulo-庚酸酯（34）（5：1）导致α：β比率为1：1 2,5

  DOI：

  10.1016/s0008-6215(00)90891-7

文献信息

• Antidiabetic phosphonates
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0372157A1

  公开（公告）日：1990-06-13

  Phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, therey lowering glu­cose levels in mammals. These phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphonates are also dis­closed.

  已公开的膦酸盐可刺激果糖-1,6-二磷酸酶并抑制 6-磷酸果糖-1-激酶，从而降低哺乳动物体内的葡萄糖水平。因此，这些膦酸盐可用于治疗高血糖和/或糖尿病。此外，还公开了膦酸盐的合成工艺。
• Formation of chiral alkoxy dienes in Wittig/Michael reactions of 2,3,5-tri-O-benzyl-D-arabinose
  作者：Allen B. Reitz、Alfonzo D. Jordan、Bruce E. Maryanoff

  DOI：10.1021/jo00230a031

  日期：1987.10
• US4945158A
  申请人：——

  公开号：US4945158A

  公开（公告）日：1990-07-31
• Synthesis of C-arabinofuranosyl compounds. Phosphonate and carboxylate isosteres of d-arabinose 1,5-bisphosphate
  作者：Bruce E. Maryanoff、Samuel O. Nortey、Ruth R. Inners、Susan A. Campbell、Allen B. Reitz、Dennis Liotta

  DOI：10.1016/s0008-6215(00)90891-7

  日期：1987.12

  key importance in the successful synthesis of a phosphonate analog of β- d -arabinose 1,5-bisphosphate ( 1 ), namely, 2,5-anhydro-1-deoxy-1-phosphono- d -glucitol 6-phosphate ( 4 ), whith high stereoselectivity. By contrast, condensation of the sodium salt of tetraethyl methylenediphosphonate and 2,3,5-tri- O -benzyl- d -arabinose ( 7 ) gave a phosphonate compound slightly enriched in the 2,5-anhydro-

  摘要用N-溴代琥珀酰亚胺对3,4,6-tri-O-苄基-1,2-二脱氧-d-阿拉伯糖-hex-1-烯醇进行亲电介导的环化反应主要产生2,5-脱水-3,4,6 -三-O-苄基-1-溴-1-脱氧-d-葡萄糖醇（10）。在成功合成β-d-阿拉伯糖1,5-双磷酸酯（1）的膦酸酯类似物（即2,5-脱水-1-脱氧1-膦酰基-d-）的成功合成中，这一显然由动力学控制的反应至关重要。具有高立体选择性的6-磷酸葡萄糖醇（4）。相反，将亚甲基二膦酸四乙酯的钠盐与2,3,5-三-O-苄基-d-阿拉伯糖（7）缩合，得到的膦酸酯化合物稍微富含2,5-脱水-d-甘露糖醇（α）。异构体。在稳定的phosphor烷与7的维蒂希-迈克尔反应中，α异构体占优势。由于甲基3,6-脱水-4,5的平衡，7-三-O-苄基-2-脱氧-d-甘油-d-半乳糖-（33）和-d-gulo-庚酸酯（34）（5：1）导致α：β比率为1：1 2,5
• Stereospecific synthesis of 5-phospho-α-d-arabinosyl-C-phosphonophosphate (pACpp): a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-d-arabinosyl pyrophosphate (pApp)
  作者：Philip McGurk、Grace X Chang、Todd L Lowary、Michael McNeil、Robert A Field

  DOI：10.1016/s0040-4039(01)00118-6

  日期：2001.3

  The stereospecific synthesis of 5-phospho-alpha -D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro. (C) 2001 Elsevier Science Ltd. All rights reserved.