((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester | 130465-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester
• 英文别名: [(2R,3R,4S,5S)-5-(diethoxyphosphorylmethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol
• CAS: 130465-01-9
• 化学式: C₂₄H₃₃O₇P
• 分子量: 464.496
• InChiKey: BBVCTJLXAYCMSU-MOUTVQLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((2S,3S,4R,5R)-3,4-Bis-benzyloxy-5-hydroxymethyl-tetrahydro-furan-2-ylmethyl)-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 N,N'-羰基二咪唑 作用下， 以 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2S,3S,4R,5R)-5-[[oxido(diphenoxy)phosphaniumyl]oxymethyl]-3,4-bis(phenylmethoxy)oxolan-2-yl]methyl-[oxido(phenoxy)phosphoryl]oxyphosphinate
  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：

  2,5-脱水-1-O-三苯甲基-D-甘露醇 在 甲醇 、 N-碘代丁二酰亚胺 、 硫酸 、 sodium 、 sodium hydride 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 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

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。
• US4945158A
  申请人：——

  公开号：US4945158A

  公开（公告）日：1990-07-31
• 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.