1(R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2,3-O-isopropylideneuridin-5-yl)phosphono]prop-2-enyl}-1,4-imino-D-galactitol | 884507-81-7

• 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: 1(R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2,3-O-isopropylideneuridin-5-yl)phosphono]prop-2-enyl}-1,4-imino-D-galactitol
• 英文别名: (1R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2',3'-O-isopropylideneuridin-5'-yl)phosphono]-2-propen-1-yl}-1,4-imino-D-galactitol；benzyl (2R,3S,4S,5S)-2-[(E)-3-[[(3aR,4R,6R,6aR)-4-(2,4-dioxopyrimidin-1-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-ethoxy-oxidophosphaniumyl]prop-2-enyl]-5-[(1S)-1,2-bis(phenylmethoxy)ethyl]-3,4-bis(phenylmethoxy)pyrrolidine-1-carboxylate
• CAS: 884507-81-7
• 化学式: C₅₉H₆₆N₃O₁₄P
• 分子量: 1072.16
• InChiKey: PDXUZMMKTPMAHF-COELTHQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  77
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  185
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  1(R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2,3-O-isopropylideneuridin-5-yl)phosphono]prop-2-enyl}-1,4-imino-D-galactitol 在 三氯化硼 、 水 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 以52%的产率得到1(R)-1,4-dideoxy-1-C-{3-[(ethyl)(uridin-5-yl)phosphono]prop-2-enyl}-1,4-imino-D-galactitol
  参考文献：
  名称：

  聚合和立体选择性合成含氨基糖的Gal f和UDP-Gal f缩氨酸：评价为UDP-Gal突变酶的抑制剂。

  摘要：

  的合成UDP-Gal的˚F类似物掺入1,4-二脱氧-1,4-亚氨基- d -galactitol骨架α联通过3C-系绳和一系列相关吡咯烷呋喃半乳糖模拟了的被报告的到UMP。这些化合物是通过甲硅烷基化的亲核试剂与N- Cbz葡糖呋喃糖胺的高度立体选择性反应而获得的，N- Cbz葡糖呋喃糖胺提供了1,2-顺式立体化学的相应开链产物，这是从Kobayashi的开创性研究中预测到的。这些中间体，得到α-环化Ç -glycosides亚氨基呋喃半乳糖携带各种官能团中的糖苷配基的。进一步阐述α- C脱保护后，通过与间质5'-乙烯基乙烯基膦酸酯的交叉复分解反应，生成-烯丙基取代的衍生物，得到所需的原始UDP-Gal f缩影。使用BCl 3切割亚氨基糖组分中的苄基醚保护基对合成计划的成功至关重要。几个新的1,4-二去氧-1,4-亚氨基的d -galactitol衍生物评价为从UGM（UDP-吡喃半乳糖变位酶）的抑制剂的大肠杆菌;

  DOI：

  10.1021/jo8001134
• 作为产物：
  描述：

  (1R)-1-C-allyl-2,3,5,6-tetra-O-benzyl-1-benzyloxycarbonylamino-1-deoxy-D-glucitol 在 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 61.0h， 生成 1(R)-2,3,5,6-tetra-O-benzyl-N-benzyloxycarbonyl-1,4-dideoxy-1-C-{3-[(ethyl)(2,3-O-isopropylideneuridin-5-yl)phosphono]prop-2-enyl}-1,4-imino-D-galactitol
  参考文献：
  名称：

  Stereoselective Synthesis of α-C-Substituted 1,4-Dideoxy-1,4-imino-d-galactitols. Toward Original UDP-Galf Mimics via Cross-Metathesis

  摘要：

  Various alpha-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols were prepared efficiently from 1-O-acetyl-2,3,5,6-tetra-O-benzyl-D-glucofuranose by a four-step sequence involving as the key step the highly syn-selective TMSOTf-catalyzed addition of silylated nucleophiles to a glycofuranosylamine. Cross-metathesis of the alpha-C-allylated iminogalactofuranose derivative with an original uridin-5'-yl vinylphosphonate led to novel UDP-galactofuranose mimics. Such compounds are of interest as potential inhibitors of the mycobacterial galactan biosynthesis pathway.

  DOI：

  10.1021/ol053078z

文献信息

• Convergent and Stereoselective Synthesis of Iminosugar-Containing Gal<i>f</i> and UDP-Gal<i>f</i> Mimicks:  Evaluation as Inhibitors of UDP-Gal Mutase
  作者：Virginie Liautard、Valérie Desvergnes、Kenji Itoh、Hung-wen Liu、Olivier R. Martin

  DOI：10.1021/jo8001134

  日期：2008.4.1

  which afforded the corresponding open-chain product with a 1,2-syn stereochemistry, as predicted from pionneering studies from Kobayashi. Cyclization of these intermediates afforded α-C-glycosides of imino-galactofuranose carrying various functional groups in the aglycone. Further elaboration of the α-C-allyl substituted derivative by cross-metathesis with a uridin-5‘-yl vinylphosphonate provided, after

  的合成UDP-Gal的˚F类似物掺入1,4-二脱氧-1,4-亚氨基- d -galactitol骨架α联通过3C-系绳和一系列相关吡咯烷呋喃半乳糖模拟了的被报告的到UMP。这些化合物是通过甲硅烷基化的亲核试剂与N- Cbz葡糖呋喃糖胺的高度立体选择性反应而获得的，N- Cbz葡糖呋喃糖胺提供了1,2-顺式立体化学的相应开链产物，这是从Kobayashi的开创性研究中预测到的。这些中间体，得到α-环化Ç -glycosides亚氨基呋喃半乳糖携带各种官能团中的糖苷配基的。进一步阐述α- C脱保护后，通过与间质5'-乙烯基乙烯基膦酸酯的交叉复分解反应，生成-烯丙基取代的衍生物，得到所需的原始UDP-Gal f缩影。使用BCl 3切割亚氨基糖组分中的苄基醚保护基对合成计划的成功至关重要。几个新的1,4-二去氧-1,4-亚氨基的d -galactitol衍生物评价为从UGM（UDP-吡喃半乳糖变位酶）的抑制剂的大肠杆菌;
• Stereoselective Synthesis of α-<i>C</i>-Substituted 1,4-Dideoxy-1,4-imino-<scp>d</scp>-galactitols. Toward Original UDP-Gal<i>f</i> Mimics via Cross-Metathesis
  作者：Virginie Liautard、Valérie Desvergnes、Olivier R. Martin

  DOI：10.1021/ol053078z

  日期：2006.3.1

  Various alpha-C-substituted 1,4-dideoxy-1,4-imino-D-galactitols were prepared efficiently from 1-O-acetyl-2,3,5,6-tetra-O-benzyl-D-glucofuranose by a four-step sequence involving as the key step the highly syn-selective TMSOTf-catalyzed addition of silylated nucleophiles to a glycofuranosylamine. Cross-metathesis of the alpha-C-allylated iminogalactofuranose derivative with an original uridin-5'-yl vinylphosphonate led to novel UDP-galactofuranose mimics. Such compounds are of interest as potential inhibitors of the mycobacterial galactan biosynthesis pathway.