methyl (5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate | 1219718-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
• 英文别名: dibutyl [methyl (7,8,9-tri-O-acetyl-5-amino-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate] phosphate；methyl (3aR,4R,6S,7aS)-6-[dibutoxy(oxido)phosphaniumyl]oxy-2-oxo-4-[(1S,2R)-1,2,3-triacetyloxypropyl]-3a,4,7,7a-tetrahydro-3H-pyrano[3,4-d][1,3]oxazole-6-carboxylate
• CAS: 1219718-01-0
• 化学式: C₂₅H₄₀NO₁₅P
• 分子量: 625.564
• InChiKey: JUCGQLDIZFAREM-VPLWQFIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  42
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  methyl (5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 mineral oil 为溶剂， 反应 1.83h， 生成 methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-2-C-(2-propenyl)-D-erythro-L-gluco-nononate
  参考文献：
  名称：

  Stereoselective, Electrophilic α-C-Sialidation

  摘要：

  5-N-Acetyl-5-N,4-O-oxazolidinone protected alpha- and beta-sialyl phosphates react with allyltributylstannane and a variety of trimethylsilyl enol ethers to give alpha-sialyl C-glycosides in high yield and excellent selectivity. Elimination to give the 2,3-glycal is minimized by the presence of the oxazolidinone ring. The oxazolidinone ring can be subsequently cleaved under mild conditions at room temperature leaving in place the native acetamide group.

  DOI：

  10.1021/ol300255q
• 作为产物：
  描述：

  methyl (4S,5R,6R)-5-amino-4-hydroxy-2-(4-methylphenyl)sulfanyl-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate 在 吡啶 、 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 methyl (5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
  参考文献：
  名称：

  Studies on the sialylation of galactoses with different C-5 modified sialyl donors

  摘要：

  Synthetic sialylated glycans provide useful tools to study carbohydrate-mediated biological recognition; however chemical sialylation is the most challenging practice in preparative carbohydrate chemistry, which is often associated with low yields and poor stereoselectivity. Herein, we conducted extensive studies on sialylation with five types of 5-N-modified sialyl donors and four types of galactosyl acceptors. Our studies have shown that a good combination between the donor and the acceptor seems necessary to achieve high yield and stereoselectivity. None of the donors or acceptors showed 'universal' utility toward the sialylation reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.08.007

文献信息

• Highly Alpha-Selective Sialyl Phosphate Donors for Efficient Preparation of Natural Sialosides
  作者：Che-Hsiung Hsu、Kuo-Ching Chu、Yih-Shyan Lin、Jeng-Liang Han、Yu-Shiang Peng、Chien-Tai Ren、Chung-Yi Wu、Chi-Huey Wong

  DOI：10.1002/chem.200903035

  日期：2010.2.8

  Hubble, bubble, toil, and trouble: The use of a new sialyl phosphate donor allows the stereoselective, one‐pot multicomponent synthesis of α‐sialooligosaccharides (see scheme).

  哈勃，气泡，辛劳和麻烦：使用新的唾液酸磷酸酯供体可以立体选择性地单锅多组分合成α-唾液寡糖（参见方案）。