3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose | 59541-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
• 英文别名: 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranose-5-ulose；1-[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-phenylmethoxyethanone
• CAS: 59541-28-5
• 化学式: C₂₃H₂₆O₆
• 分子量: 398.456
• InChiKey: NVQMEAJONUXZKW-CIAFKFPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose 在 甲基戊酰氯 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 反应 7.0h， 生成 3,6-di-O-benzyl-5-deoxy-5-dimethoxyphosphinyl-1,2-O-isopropylidene-β-L-idofuranose
  参考文献：
  名称：

  A New Route for Preparation of 5-Deoxy-5-hydroxyphosphinyl-D-gluco- and L-idopyranose Derivatives

  摘要：

  DOI：

  10.3987/com-98-s(h)53
• 作为产物：
  描述：

  1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 3,6-di-O-benzyl-1,2-O-isopropylidene-α-D-xylo-hexofuranos-5-ulose
  参考文献：
  名称：

  Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)

  摘要：

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00235-0

文献信息

• α-Geminal Dihydroxymethyl Piperidine and Pyrrolidine Iminosugars: Synthesis, Conformational Analysis, Glycosidase Inhibitory Activity, and Molecular Docking Studies
  作者：Nitin J. Pawar、Vijay Singh Parihar、Sanjay T. Chavan、Rakesh Joshi、Pranaya V. Joshi、Sushma G. Sabharwal、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1021/jo3009534

  日期：2012.9.21

  with C5-amino gave 4C-dihydroxymethyl pyrrolidine iminosugars 1b and 1c, respectively. On the basis of the 1H NMR studies, the conformations of 2a/2b were assigned as 4C1 and that of 2c as 1C4. The glycosidase inhibitory activities of all five iminosugars were studied with various glycosidase enzymes and compared with natural d-gluco-1-deoxynojirimycin (DNJ). All the five compounds were found to be potent

  二氯甲基锂与适当保护的5-酮-六呋喃糖酶的Jocic-Reeve和Corey-Link型反应，然后用叠氮化钠和硼氢化钠处理，得到具有所需双键二羟甲基基团的5-叠氮基-5-羟甲基取代的六呋喃糖酶7a - c。去除保护基并将C-1异头碳转化为游离半缩醛，然后分子内还原性氨基环化并原位生成C5-氨基官能团，得到相应的5C-二羟甲基哌啶亚氨基糖2a – c。或者，去除7b和7c中的保护基将C 1-异头碳切断，得到C 2-醛，然后用C 5-氨基进行分子内还原性氨基环化，分别得到4 C-二羟甲基吡咯烷亚氨基糖1b和1c。根据1 H NMR研究，将2a / 2b的构象指定为4 C 1，将2c的构象指定为1 C 4。所有五个亚氨基糖类的糖苷酶抑制活性进行了研究各种糖苷酶和天然相比d -葡萄糖-1-脱氧野oji霉素（DNJ）。发现所有这五种化合物都是水稻α-葡萄糖苷酶的有效抑制剂，其K i和IC 50值在纳
• Synthesis of 1,2,4-tri-O-acetyl-3,6-di-O-benzyl-5-deoxy-5-C-[(S)-phenylphosphinyl]-β-d-glucopyranose: The first gluco type of hexopyranose derivative having phosphorus in the hemiacetal ring
  作者：Hiroshi Yamamoto、Chikako Hosoyamada、Heizan Kawamoto、Saburo Inokawa、Mitsuji Yamashita、Margaret-Ann Armour、Tom T. Nakashima

  DOI：10.1016/s0008-6215(00)88059-3

  日期：1982.4
• Synthesis of α-azido aldehydes. Stereoselective formal access to the immunosuppressant myriocin
  作者：Sandrine Deloisy、Ton That Thang、Alain Olesker、Gabor Lukacs

  DOI：10.1016/s0040-4039(00)76967-x

  日期：1994.7

  Stereoselective preparation of an acyclic alpha-azido aldehyde permitted acces
• Deloisy, Sandrine; Thang, Ton That; Olesker, Alain, Bulletin de la Societe Chimique de France, 1996, vol. 133, # 6, p. 581 - 585
  作者：Deloisy, Sandrine、Thang, Ton That、Olesker, Alain、Lukacs, Gabor

  DOI：——

  日期：——
• Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (α-hydroxyphosphonates)
  作者：Tadashi Hanaya、Ken-ichi Sugiyama、Heizan Kawamoto、Hiroshi Yamamoto

  DOI：10.1016/s0008-6215(03)00235-0

  日期：2003.7

  The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed. (C) 2003 Elsevier Ltd. All rights reserved.