1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose | 357940-81-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose
• 英文别名: (2S,3S,4S,5R,6R)-2-(benzenesulfinyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 357940-81-9
• 化学式: C₄₀H₄₀O₆S
• 分子量: 648.82
• InChiKey: SZCBPJJRURAJJH-XKNMPSQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2,3,4-三-O-苄基-α-D-吡喃葡萄糖苷 、 1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose 在 5 Angstroem MS 、 硫酸酯 、 zirconium(IV) oxide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以85%的产率得到methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-mannopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Novel stereocontrolled α- and β-glycosidations of mannopyranosyl sulfoxides using environmentally benign heterogeneous solid acids

  摘要：

  The environmentally benign and stereocontrolled glycosidations of mannopyranosyl sulfoxides and alcohols using a heterogeneous solid acid, Nafion-H or sulfated zirconia (SO4/ZrO2) as a new activator for the direct syntheses of both the alpha- and beta -mannopyranosides have been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00674-8
• 作为产物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-mannopyranoside 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose 、 1-deoxy-2,3,4.6-tetrakis-O-phenylmethyl-1-phenylsulfinyl-mannopyranose
  参考文献：
  名称：

  [EN] METHODS AND COMPOSITIONS FOR ENZYME-SPECIFIC ACTIVATION OF CARBOHYDRATE-CONJUGATED PRODRUGS
  [FR] METHODES ET COMPOSITIONS D'ACTIVATION SPECIFIQUE D'ENZYME DE PROMEDICAMENTS CONJUGUES A DES GLUCIDES

  摘要：

  公开号：

  WO2006042056A3

文献信息

• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.
• Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides
  作者：Kazunobu Toshima、Hideyuki Nagai、Ken-ichi Kasumi、Kanako Kawahara、Shuichi Matsumura

  DOI：10.1016/j.tet.2004.04.071

  日期：2004.6

  Novel alpha- and beta-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl alpha-fluorides with several alcohols using SO4/ZrO2 in MeCN proceeded alpha-stereoselectively, while those with the same activator in the presence of MS 5A in Et2O occurred with beta-stereo selectivity. Thus, both the alpha- and beta-manno- and 2-deoxyglucopyranosides were effectively obtained by the present glycosidations. (C) 2004 Elsevier Ltd. All rights reserved.
• Methods and Compositions for Enzyme-Specific Activation of Carbohydrate-Conjugated Prodrugs
  申请人：Sun Duxin

  公开号：US20080312162A1

  公开（公告）日：2008-12-18

  Methods for the targeted activation of prodrugs by enzymes, which cleave a linkage between a carbohydrate conjugate and a drug. Means to target the activation of prodrugs to specific cells by linking the enzyme to an antibody molecule. Carbohydrate conjugates of geldanamycin.
• Novel stereocontrolled α- and β-glycosidations of mannopyranosyl sulfoxides using environmentally benign heterogeneous solid acids
  作者：Hideyuki Nagai、Kanako Kawahara、Shuichi Matsumura、Kazunobu Toshima

  DOI：10.1016/s0040-4039(01)00674-8

  日期：2001.6

  The environmentally benign and stereocontrolled glycosidations of mannopyranosyl sulfoxides and alcohols using a heterogeneous solid acid, Nafion-H or sulfated zirconia (SO4/ZrO2) as a new activator for the direct syntheses of both the alpha- and beta -mannopyranosides have been developed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• [EN] METHODS AND COMPOSITIONS FOR ENZYME-SPECIFIC ACTIVATION OF CARBOHYDRATE-CONJUGATED PRODRUGS<br/>[FR] METHODES ET COMPOSITIONS D'ACTIVATION SPECIFIQUE D'ENZYME DE PROMEDICAMENTS CONJUGUES A DES GLUCIDES
  申请人：UNIV OHIO STATE

  公开号：WO2006042056A3

  公开（公告）日：2006-10-26