(1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranosyl) benzyl phthalate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranosyl) benzyl phthalate
• 英文别名: 2-O-[(3aR,6R,6aR)-4,6-bis(benzoyloxymethyl)-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-yl] 1-O-benzyl benzene-1,2-dicarboxylate
• 化学式: C₃₈H₃₄O₁₁
• 分子量: 666.681
• InChiKey: NMHFHRBEAUHHQA-RJTOJIECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranosyl) benzyl phthalate 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.67h， 生成
  参考文献：
  名称：

  (+)-5-硫代蔗糖和(+)-5-硫代异蔗糖的立体选择性合成

  摘要：

  (+)-5-Thiosucrose 1是蔗糖的新型等排硫类似物，首次通过间接 β- D-呋喃果糖苷化（包括选择性 β- D -psicofuranosidation）立体选择性合成，随后在呋喃糖环上的 C-3 位置。受保护的 5-硫代-D-葡萄糖与D-呋喃喃糖基供体的糖苷化提供 β- D-呋喃酮糖基 5-硫代-α- D-吡喃葡萄糖苷，而与D-呋喃果糖基供体的糖苷化生成 α- D-呋喃果糖基 5-硫代-α- D-吡喃葡萄糖苷。糖基供体和受体的两个异头立体中心被正确控制，以提供糖基化中四种可能的异头异构体中的单一二糖。所得二糖的转化分别以优异的产率得到 (+)-5-硫代蔗糖1和 (+)-5-硫代异蔗糖2。还检测了1和2在体外对 α-葡萄糖苷酶的抑制活性。

  DOI：

  10.1039/d0ra01033b
• 作为产物：
  描述：

  1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranose 、 邻苯二甲酸单苄酯 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以95%的产率得到(1,6-di-O-benzoyl-3,4-O-isopropylidene-D-psicofuranosyl) benzyl phthalate
  参考文献：
  名称：

  Chemical synthesis of β-d-psicofuranosyl disaccharides

  摘要：

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.030

文献信息

• Synthesis of (+)-sucrose via β-d-psicofuranosylation
  作者：Jun’ichi Uenishi、Atsushi Ueda

  DOI：10.1016/j.tetasy.2008.09.008

  日期：2008.9

  Despite the difficulty of direct beta-furanosylation with D-fructose, the synthesis of beta-D-fructofuranosyl alpha-D-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via beta-selective D-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. D-Psicofuranosyl donor 10 was prepared in eight steps from D-ribose monoacetomide 3 in excellent yield. (C) 2008 Elsevier Ltd. All rights reserved.
• β-Selective D-Psicofuranosylation of Pyrimidine Bases and Thiols
  作者：Atsushi Ueda、Yuri Nishimura、Yui Makura、Masakazu Tanaka、Jun'ichi Uenishi

  DOI：10.3987/com-18-s(t)42

  日期：——

  N-Glycosidation of D-psicofuranosyl donor 1 with pyrimidine bases took place beta-selectively in a beta/alpha -ratio of 8:1 similar to 7:1. For S-glycosidation, 3,4-O-(3-pentylidene)-protected D-psicofuranosyl donor 15 was effective to increase beta-selectivity up to 7:1.
• Stereoselective β-D-Psicofuranosylation and Synthesis of β-D-Psicofuranosylceramide
  作者：Jun'ichi Uenishi、Atsushi Ueda

  DOI：10.3987/com-08-s(f)115

  日期：——

  Psicofurarlosylations of alcohols and phenol 3a-e with benzyl D-psicosyl phthalate 2 occurred on the beta-face to give beta-D-psicoside 4a-e in excellent yields. The reaction of ceramide 5 with 2 and deprotections of acetonide and three benzoates of the resulting glycoside afforded beta-D-psicosylceramide 1.
• Chemical synthesis of β-d-psicofuranosyl disaccharides
  作者：Atsushi Ueda、Takanori Yamashita、Jun’ichi Uenishi

  DOI：10.1016/j.carres.2010.05.030

  日期：2010.8

  Disaccharides composed of a beta-D-psicofuranosyl unit were prepared by the glycosylation reaction of monosaccharide acceptors including three 23,4,6-tetra-O-protected hexopyranoses with a D-psicofuranosyl benzyl phthalate derivative (4). A beta-D-psicofuranosidic bond was formed by the TMSOTf-promoted reaction with high selectivity. Removal of the O-protecting groups from the resulting a-D-hexopyranosyl beta-D-psicofuranosides furnished the first chemical synthesis of alpha-D-gluco-, alpha-D-galacto-, and et-D-mannopyranosyl beta-D-psicofuranosides. The common beta-D-psicofuranosyl donor 4 was derived efficiently from D-psicose in five steps. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of (+)-5-thiosucrose and (+)-5-thioisosucrose
  作者：Atsushi Ueda、Jinhong Pi、Yui Makura、Masakazu Tanaka、Jun'ichi Uenishi

  DOI：10.1039/d0ra01033b

  日期：——

  stereo-inversion of the secondary hydroxy group at the C-3 position on the furanose ring. Glycosidation of protected 5-thio-D-glucose with a D-psicofuranosyl donor provided β-D-psicofuranosyl 5-thio-α-D-glucopyranoside and that with D-fructofuranosyl donor gave α-D-fructofuranosyl 5-thio-α-D-glucopyranoside. Two anomeric stereocenters of the glycosyl donor and acceptor were controlled correctly to

  (+)-5-Thiosucrose 1是蔗糖的新型等排硫类似物，首次通过间接 β- D-呋喃果糖苷化（包括选择性 β- D -psicofuranosidation）立体选择性合成，随后在呋喃糖环上的 C-3 位置。受保护的 5-硫代-D-葡萄糖与D-呋喃喃糖基供体的糖苷化提供 β- D-呋喃酮糖基 5-硫代-α- D-吡喃葡萄糖苷，而与D-呋喃果糖基供体的糖苷化生成 α- D-呋喃果糖基 5-硫代-α- D-吡喃葡萄糖苷。糖基供体和受体的两个异头立体中心被正确控制，以提供糖基化中四种可能的异头异构体中的单一二糖。所得二糖的转化分别以优异的产率得到 (+)-5-硫代蔗糖1和 (+)-5-硫代异蔗糖2。还检测了1和2在体外对 α-葡萄糖苷酶的抑制活性。