8-(methoxycarbonyl)octyl α-D-mannoipyranoside | 77666-97-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-(methoxycarbonyl)octyl α-D-mannoipyranoside
• 英文别名: 8-(Methoxycarbonyl)octyl α-D-mannopyranoside；8-methoxycarbonyloctyl α-D-mannopyranoside；8-methoxycarbonyloctyl-α-D-mannopyranoside；Methyl Ester Octyl Alpha-1o-D-Mannopyrannoside；methyl 9-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxynonanoate
• CAS: 77666-97-8
• 化学式: C₁₆H₃₀O₈
• 分子量: 350.409
• InChiKey: ZJZBQHWSENWEMY-VMMWWAARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-(methoxycarbonyl)octyl α-D-mannoipyranoside 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.0h， 生成 9-(α-D-mannopyranosyloxy)nonanoic acid
  参考文献：
  名称：

  精氨酸-加压素的新型糖结合物的合成和抗利尿活性。

  摘要：

  在pH 9.1缓冲液中，将精氨酸-加压素（AVP）与各种酰基叠氮化物（2a-j）酰化，以在酪氨酸侧链上通过间隔基臂用碳水化合物修饰AVP衍生物（11a-j）。还使用二环己基碳二亚胺和1-羟基苯并三唑作为偶联剂，由AVP和羧酸（3a-e）合成了在N末端酰胺（12a-e）处修饰的AVP糖共轭物。类似物（11a-j）的体内抗利尿活性高于AVP。AVP和糖缀合物（12a-e）在大鼠血浆中稳定。另一方面，发现糖缀合物（11a-i）根据一级动力学容易转化为AVP。因此，11a-j被认为是AVP的前药。

  DOI：

  10.1248/cpb.46.1530
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 4 A molecular sieve 、 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 22.0h， 生成 8-(methoxycarbonyl)octyl α-D-mannoipyranoside
  参考文献：
  名称：

  对应于溶酶体酶高甘露糖链端基的磷酸化三甘露糖苷的合成

  摘要：

  适当保护的8-甲氧基羰基辛基α-D-甘露糖吡喃糖苷与2-O-乙酰-3,4,6-三-O-苄基-α-D-甘露吡喃糖酰氯的糖基化提供了α-D-Manp-（1-- --2）-alpha-D-Man，alpha-D-Manp-（1 ---- 3）-alpha-D-Man和alpha-D-Manp-（1 ---- 6）-alpha-D -Man衍生物，通过O-脱乙酰基作用释放2'-羟基。在标准糖基化条件下，通过与易于获得的2,3,4-三-O-乙酰基-6-O-二苯氧基磷酰基-α-D-甘露吡喃糖基溴反应，可实现末端D-甘露糖6-磷酸残基的添加。常规脱保护提供了α-D-Manp-（1 ---- 2）-α-D-Manp-（1 ---- 2）-α-D-Man，α-D- Manp-（1 ---- 2）-alpha-D-Manp-（1 ---- 3）-alpha-D-Man，

  DOI：

  10.1016/s0008-6215(00)90077-6

文献信息

• Preparation of 8-methoxycarbonyloctyl glycosides of α-d-mannopyranose, 2-O-α-mannopyranosyl-α-d-mannopyranose, β-d-galactofuranose, and 3-O-β-d-galactofuranosyl-α-d-mannopyranose
  作者：David S. Tsui、Philip A.J. Gorin

  DOI：10.1016/s0008-6215(00)90094-6

  日期：1986.11

  with the general structure mono-(or di-)saccharide-lipid spacer-protein having possible antigenic and immunogenic activity in respect to infection with Trypanosoma cruzi. Tri-O-acetyl-1,2-O-(1-methoxyethylidene) derivatives of D-mannopyranose and D-galactofuranose were treated with alcohols in the presence and absence of mercuric bromide to give orthoesters which rearranged into glycosides.

  制备了α-D-甘露吡喃糖，2-O-α-甘露吡喃糖基-α-D-甘露吡喃糖，β-D-半乳糖呋喃糖和3-O-β-D-半乳糖呋喃糖基α-D-甘露吡喃糖的8-甲氧羰基辛基糖苷。作为合成具有一般结构的复合物的中间体，单（或二）糖-脂质间隔蛋白对克鲁斯锥虫的感染具有可能的抗原和免疫原活性。在存在和不存在溴化汞的情况下，用醇处理D-甘露吡喃糖和D-半乳糖呋喃糖的三-O-乙酰基-1,2-O-（1-甲氧基亚乙基）衍生物，得到原酸酯，其重新排列成糖苷。
• Synthesis and Antidiuretic Activities of Novel Glycoconjugates of Arginine-Vasopressin.
  作者：Hiroshi SUSAKI、Kokichi SUZUKI、Masahiro IKEDA、Harutami YAMADA、Hiroshi K. WATANABE

  DOI：10.1248/cpb.46.1530

  日期：——

  Arginine-vasopressin (AVP) was acylated with various acyl azides (2a-j) in pH 9.1 buffer to give AVP derivatives (11a-j) modified at the tyrosine side chain with a carbohydrate via a spacer arm. Glycoconjugates of AVP modified at the N-terminal amide (12a-e) were also synthesized from AVP and carboxylic acids (3a-e) using dicyclohexylcarbodiimide and 1-hydroxybenzotriazole as coupling agent. Analogues

  在pH 9.1缓冲液中，将精氨酸-加压素（AVP）与各种酰基叠氮化物（2a-j）酰化，以在酪氨酸侧链上通过间隔基臂用碳水化合物修饰AVP衍生物（11a-j）。还使用二环己基碳二亚胺和1-羟基苯并三唑作为偶联剂，由AVP和羧酸（3a-e）合成了在N末端酰胺（12a-e）处修饰的AVP糖共轭物。类似物（11a-j）的体内抗利尿活性高于AVP。AVP和糖缀合物（12a-e）在大鼠血浆中稳定。另一方面，发现糖缀合物（11a-i）根据一级动力学容易转化为AVP。因此，11a-j被认为是AVP的前药。
• Synthesis of phosphorylated trimannosides corresponding to end groups of the high-mannose chains of lysosomal enzymes
  作者：Om P. Srivastava、Ole Hindsgaul

  DOI：10.1016/s0008-6215(00)90077-6

  日期：1987.4

  alpha-D-Manp-(1----6)-alpha-D-Man derivatives from which the 2'-hydroxyl group was liberated by O-deacetylation. Addition of the terminal D-mannose 6-phosphate residues was achieved by reaction with the readily accessible 2,3,4-tri-O-acetyl-6-O-diphenoxyphosphoryl-alpha-D-mannopyranosyl bromide under standard glycosylation conditions. Conventional deprotection provided the terminal 6"-phosphate of alpha-D-

  适当保护的8-甲氧基羰基辛基α-D-甘露糖吡喃糖苷与2-O-乙酰-3,4,6-三-O-苄基-α-D-甘露吡喃糖酰氯的糖基化提供了α-D-Manp-（1-- --2）-alpha-D-Man，alpha-D-Manp-（1 ---- 3）-alpha-D-Man和alpha-D-Manp-（1 ---- 6）-alpha-D -Man衍生物，通过O-脱乙酰基作用释放2'-羟基。在标准糖基化条件下，通过与易于获得的2,3,4-三-O-乙酰基-6-O-二苯氧基磷酰基-α-D-甘露吡喃糖基溴反应，可实现末端D-甘露糖6-磷酸残基的添加。常规脱保护提供了α-D-Manp-（1 ---- 2）-α-D-Manp-（1 ---- 2）-α-D-Man，α-D- Manp-（1 ---- 2）-alpha-D-Manp-（1 ---- 3）-alpha-D-Man，
• NEPHROTROPIC DRUGS
  申请人：Drug Delivery System Institute, Ltd.

  公开号：EP0953357A1

  公开（公告）日：1999-11-03

  Disclosed are a drug having renal selectivity and a drug carrier for specifically transporting a drug supported thereon to a kidney. A segment structure specifically recognizable in the kidney is utilized. More specifically, since a segment structure represented by formula (I) is kidney-oriented, introduction of a drug into a molecule having the segment structure can provide a renal targeting drug. A compound, which has the segment structure and can support a drug thereon, can be utilized as a drug carrier which can specifically transport a drug supported thereon to the kidney.         A-U-V-     (I) wherein A represents glycosyl, such as glucosyl, mannosyl, or 2-deoxy-glucosyl; U represents O, S, or NH; and V represents an aromatic hydrocarbon or a straight-chain or branched C1-18 aliphatic hydrocarbon.

  本发明涉及一种具有肾脏选择性的药物和一种药物载体，用于将支持在其上的药物专门运输到肾脏。利用在肾脏中特别可识别的片段结构。更具体地说，由式（I）表示的片段结构是以肾脏为导向的，将药物引入具有该片段结构的分子中可以提供肾脏靶向药物。具有该片段结构并能支持药物的化合物可用作药物载体，可将支持在其上的药物专门运输到肾脏。其中，A代表糖基，如葡萄糖基、甘露糖基或2-脱氧葡萄糖基；U代表O、S或NH；V代表芳香族碳氢化合物或直链或支链C1-18脂肪族碳氢化合物。
• Synthesis of ω-(methoxycarbonyl)alkyl and 9-(methoxycarbonyl)-3,6-dioxanonyl glycopyranosides for the preparation of carbohydrate-protein conjugates
  作者：Tamio Sugawara、Kunihiko Irie、Hiroyuki Iwasawa、Takayoshi Yoshikawa、Satoshi Okuno、Hiroshi K. Watanabe、Takashi Kato、Mitsuru Shibukawa、Yukio Ito

  DOI：10.1016/s0008-6215(00)90517-2

  日期：1992.6

  Omega-(Methoxycarbonyl)alkyl glycopyranosides of D-mannose having C4, C-7, C-9, C-12, and C-15 carbon chains, L-fucose and 2-acetamido-2-deoxy-D-mannose having C-7 and C-9 carbon chains. D-xylose and 2-acetamido-2-deoxy-L-fucose having a C-9 carbon chian, and 9-(methoxycarbonyl)-3,6-dioxanoyl glycopyranosides of D-mannose. 2-acetamido-2-deoxy-D-mannose, and L-fucose were' synthesized as intermediates for coupling to human serum albumin in order to examine the effect of chain length and hydrophobicity of the spacer arm on the binding specificity of lectins. 8-(Methoxycarbonyl)octyl glycosides of beta-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-Man-(1 --> 2)-alpha-D-Man, alpha-D-ManNAc-(1 --> 2)-alpha-D-Man, beta-D-GlcNAc-(1 --> 2)-alpha-D-Man, and their 6-O-positional isomers, beta-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-Man-(1 --> 6)-alpha-D-Man, alpha-D-ManNAc-(1 --> 6)-alpha-D-Man, and beta-D-GlcNAc-(1 --> 6)-alpha-D-Man, were also synthesized.