Dibenzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-phosphat | 58530-86-2

• 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: Dibenzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-phosphat
• 英文别名: 2,3,4,6-Tetraacetate 1-[bis(phenylmethyl) phosphate]-|A-D-Mannopyranose；[(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-bis(phenylmethoxy)phosphoryloxyoxan-2-yl]methyl acetate
• CAS: 58530-86-2
• 化学式: C₂₈H₃₃O₁₃P
• 分子量: 608.536
• InChiKey: OJIXCTQZEWIIFR-URYJJRPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  Dibenzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-phosphat 在 甲醇 、 sodium methylate 作用下， 生成 dibenzyl [(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate
  参考文献：
  名称：

  Mono, di and tri-mannopyranosyl phosphates as mannose-1-phosphate prodrugs for potential CDG-Ia therapy

  摘要：

  An efficient and convergent method for the synthesis of mannose-1-phosphate prodrugs is described as a potential therapy for congenital disorders of glycosylation-la (CDG-Ia). The key feature of the proposed approach is the silver assisted nucleophilic substitution of 2,3,4,6-tetra-O-protected-alpha-D-mannopyranosyl bromides with various silver phosphate salts to afford mono, di, and tri-mannopyranosyl phosphates. A preliminary biological evaluation of the synthesized phosphate prodrugs has been carried out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.074
• 作为产物：
  描述：

  银(1+)二苄基磷酸酯 、 2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 以 甲苯 为溶剂， 反应 18.0h， 以94%的产率得到Dibenzyl-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl-phosphat
  参考文献：
  名称：

  Mono, di and tri-mannopyranosyl phosphates as mannose-1-phosphate prodrugs for potential CDG-Ia therapy

  摘要：

  An efficient and convergent method for the synthesis of mannose-1-phosphate prodrugs is described as a potential therapy for congenital disorders of glycosylation-la (CDG-Ia). The key feature of the proposed approach is the silver assisted nucleophilic substitution of 2,3,4,6-tetra-O-protected-alpha-D-mannopyranosyl bromides with various silver phosphate salts to afford mono, di, and tri-mannopyranosyl phosphates. A preliminary biological evaluation of the synthesized phosphate prodrugs has been carried out. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.074

文献信息

• Reliable Synthesis of Various Nucleoside Diphosphate Glycopyranoses
  作者：Saskia Wolf、Tanja Zismann、Nathalie Lunau、Chris Meier

  DOI：10.1002/chem.200900572

  日期：2009.8.3

  A reliable and high yielding synthetic pathway for the synthesis of the biologically highly important class of nucleoside diphosphate sugars (NDP‐sugars) was developed by using various cycloSal‐nucleotides 1 and 9 as active ester building blocks. The reaction with anomerically pure pyranosyl‐1‐phosphates 2 led to the target NDP‐sugars 20–45 in a nucleophilic displacement reaction, which cleaves the

  通过使用各种环Sal-核苷酸1和9作为活性酯结构单元，开发了一种可靠且高产的合成途径，用于合成生物学上非常重要的一类核苷二磷酸糖（NDP-糖）。与端基异构体纯的吡喃糖基-1-磷酸的反应2导致目标NDP-糖20 - 45在亲核取代反应，其切割的环在端基异构体纯的形式萨尔部分。作为核苷，可使用胞苷，尿苷，胸苷，腺苷，2'-脱氧鸟苷和2'，3'-二脱氧-2'，3'-二脱氢胸苷，而D-葡萄糖，D的磷酸盐引入了半乳糖，D-甘露糖，D - N-氨基葡萄糖，D - N-半乳糖胺，D-岩藻糖，L-岩藻糖以及6-脱氧-D-果糖。
• EP2017281
  申请人：——

  公开号：——

  公开（公告）日：——
• Chemical synthesis of the innate immune modulator – bacterial d - glycero -β- d - manno- heptose-1,7-bisphosphate (HBP)
  作者：Alessio Borio、Andreas Hofinger、Paul Kosma、Alla Zamyatina

  DOI：10.1016/j.tetlet.2017.06.014

  日期：2017.7

  The bacterial metabolite and potent innate immune modulator D-glycero-beta-D-manno-heptose-1,7-bisphosphate (HBP) and its alpha-configured counterpart D-glycero-alpha-D-manno-heptose-1,7-bisphosphate were synthesized via stereoselective anomeric phosphorylation of the peracetylated D,D-heptose 7-dibenzylphosphate by exploiting different nucleophilicity of equatorial and axial lactols in the D-manno-series. We also report a novel approach for anomeric phosphorylation using. modified Mitsunobu reaction conditions and provide the first full structural characterization of HBP. The first chemical synthesis of HBP offers access to an anomerically pure structurally defined probe for biological studies and to a lead compound operating as a powerful stimulator of intracellular signaling for possible therapeutic immunomodulation. (C) 2017 Elsevier Ltd. All rights reserved.
• Efficient Synthesis of Nucleoside Diphosphate Glycopyranoses
  作者：Silke Wendicke、Svenja Warnecke、Chris Meier

  DOI：10.1002/anie.200703237

  日期：2008.2.8