2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-D-mannitol | 109065-80-7

• 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-iodo-D-mannitol
• 英文别名: (2S,3S,4R,5R)-2-(iodomethyl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 109065-80-7
• 化学式: C₂₇H₂₉IO₄
• 分子量: 544.429
• InChiKey: SPMJAXAEPYRAND-FPCALVHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-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：

  2-[(2S,3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-1,3-thiazole 在 咪唑 、 甲醇 、 sodium tetrahydroborate 、 碘 、 三苯基膦 作用下， 以 甲醇 、 乙醚 、 甲苯 、 乙腈 为溶剂， 反应 1.75h， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-iodo-D-mannitol
  参考文献：
  名称：

  A new synthetic approach to mycobacterial cell wall α-(1→5)-d-arabinofuranosyl C-oligosaccharides

  摘要：

  Three designed arabinofuranose building blocks allowed the diastereoselective synthesis of a C-disaccharide and a C-trisaccharide by Wittig olefination. The latter compound represents the first example of all-carbon linked arabinofuranotriose analogue. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00844-x

文献信息

• Stereoselectivity in the electrophile-mediated cyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy-d-arabino-hex-1-enitol. A stereocontrolled synthesis of 1-amino-2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-d-glucitol
  作者：Fillmore Freeman、Kirk D. Robarge

  DOI：10.1016/s0008-6215(00)90874-7

  日期：1987.12

  Abstract Cyclization of 2,3,5-tri-O-benzyl-1,2-dideoxy- d -arabino-hex-1-enitol (2) with mercuric acetate, mercuric trifluoroacetate, iodine, and N-bromosuccinimide gave preponderantly the allo isomer of the C-arabinofuranosyl structure. 1-Amino-2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy- d -glucitol, which is a key intermediate in the synthesis of 3-(β- d -arabinofuranosyl)pyrazole[4,3-d]pyrimidine-5

  摘要用乙酸汞，三氟乙酸汞，碘和N-溴代琥珀酰亚胺对2,3,5-三-O-苄基-1,2-二脱氧-d-阿拉伯糖醇-己-1-烯醇（2）的环化作用主要产生同素异形体C-阿拉伯呋喃糖基结构的异构体。1-氨基-2,5-脱水-3,4,6-三-O-苄基-1-脱氧-d-葡萄糖醇，是合成3-（β-d-阿拉伯呋喃糖基）吡唑的关键中间体[立体选择性地以3个步骤从2的立体收率制备了4，3-d]嘧啶-5，7-二酮（氧代甲醛B的β-d-阿拉伯糖基差向异构体）。还讨论了环化的立体化学结果。
• Stereoselectivity of electrophile-promoted cyclizations of .gamma.-hydroxyalkenes. An investigation of carbohydrate-derived and model substrates
  作者：Allen B. Reitz、Samuel O. Nortey、Bruce E. Maryanoff、Dennis Liotta、Robert Monahan

  DOI：10.1021/jo00228a009

  日期：1987.9
• REITZ, ALLEN B.;NORTEY, SAMUEL O.;MARYANOFF, BRUCE E.;LIOTTA, DENNIS;MONA+, J. ORG. CHEM., 52,(1987) N 19, 4191-4202
  作者：REITZ, ALLEN B.、NORTEY, SAMUEL O.、MARYANOFF, BRUCE E.、LIOTTA, DENNIS、MONA+

  DOI：——

  日期：——