1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside | 196868-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside
• 英文别名: 5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-ribofuranose；5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D-ribofuranoside；5'-O-tert-butyldimethylsilyl-1',2'-bis(O-isopropylidene)-D-ribofuranoside；1,2-O-isopropylidene-5-O-tert-butyldimethylsilyl-α-D-ribofuranose；5-O-(tert-Butyldimethylsilyl)-1,2-O-isopropylidene-α-D-ribofuranoside；(3aR,5R,6R,6aR)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 196868-07-2
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: WHHPDHGRRYXEHB-DDHJBXDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside 在 钯 吡啶 、 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 四丁基氟化铵 、 氢气 、 sodium methylate 、 咪唑 三氟甲磺酸盐 、 三乙胺 、 六甲基二硅氮烷 、 三氟乙酸 、 硫代氯甲酸苯酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， -78.0~20.0 ℃ 、413.68 kPa 条件下， 反应 8.0h， 生成 5'-deoxy-5'-phenyladenophostin A
  参考文献：
  名称：

  Synthesis of Adenophostin A Analogues Conjugating an Aromatic Group at the 5‘-Position as Potent IP₃ Receptor Ligands

  摘要：

  Previous structure-activity relationship studies of adenophostin A, a potent IP3 receptor agonist, led us to design the novel adenophostin A analogues 5a-c, conjugating an aromatic group at the 5'-position to develop useful IP3 receptor ligands. The common key intermediate, a D-ribosyl alpha-D-glucoside 10 alpha, was stereoselectively synthesized by a glycosidation with the 1-sulfinylglucoside donor 11, which was conformationally restricted by a 3,4-O-cyclic diketal protecting group. After introduction of an aromatic group at the 5-position of the ribose moiety, an adenine base was stereoselectively introduced at the anomeric beta-position to form 7a-c, where the tetra-O-i-butyryl donors 9a-c were significantly more effective than the corresponding O-acetyl donor. Thus, the target compounds 5a-c were synthesized via phosphorylation of the 2', 3", and 4"-hydroxyls. The potencies of compounds 5a-c for Ca2+ release were shown to be indistinguishable from that of adenophostin A, indicating that bulky substitutions at the 5'-position of adenophostin A are well-tolerated in the receptor binding. This biological activity of 5a-c can be rationalized by molecular modeling using the ligand binding domain of the IP3 receptor.

  DOI：

  10.1021/jm060310d
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-ribofuranoside
  参考文献：
  名称：

  侧链立体化学在有效的天然α-葡糖苷酶抑制剂kotalanol的α-葡糖苷酶抑制活性中的作用。第2部分

  摘要：

  为了检查kotalanol（的侧链的作用2），一种有效的天然α葡萄糖苷酶抑制剂分离自五层龙网状，上抑制活性，四个非对映体（11A - 11D）具有相反构型（小号）在C-4'位合成并评估了侧链中的α。四个中的两个（11b和11d）明显失去了对麦芽糖酶和蔗糖酶的抑制活性，而另外两个（11a和11c））在相当大程度上维持了抑制活性，响应于5'和6'位置上的羟基的立体化学的变化而显示出独特的活性。参考对这些抑制剂与hNtMGAM的计算机对接研究，合理化了不同的活性。针对异麦芽糖酶，所有四个类似物都显示出强大的抑制活性，以及2，并且11b和11d表现出酶选择性。

  DOI：

  10.1016/j.bmc.2012.09.006

文献信息

• New Approach for the Synthesis of c-di-GMP and Its Analogues
  作者：Bernd Giese、Nicolas Amiot、Karine Heintz

  DOI：10.1055/s-2006-950361

  日期：——

  The synthesis of cyclic bis(3`-5`)diguanylic acid (c-di-GMP) by using a new flexible approach is reported. The flexibility of the method is exemplified by the synthesis of base-modified analogues that will find applications in the elucidation of c-di-GMP biological modes of action.

  报道了采用一种新的灵活方法合成环状双(3`-5`)二鸟苷酸(c-di-GMP)。该方法的灵活性体现在碱基修饰类似物的合成中，这些类似物将在阐明 c-di-GMP 生物作用模式中得到应用。
• Synthesis of alkylcarbonate analogs of O-acetyl-ADP-ribose
  作者：Marcela Dvorakova、Radim Nencka、Milan Dejmek、Eva Zbornikova、Anna Brezinova、Marie Pribylova、Radek Pohl、Marie E. Migaud、Tomas Vanek

  DOI：10.1039/c3ob41016a

  日期：——

  The non-hydrolyzable alkylcarbonate analogs of O-acetyl-ADP-ribose have been synthesized from the phosphorylated ribose derivatives after coupling with AMP morpholidate promoted by mechanical grinding. The analogs were assessed for their ability to inhibit the human sirtuin homolog SIRT1.

  在机械研磨的促进下，O-乙酰基-ADP-核糖与 AMP 吗啉烷酸酯偶联，从磷酸化核糖衍生物中合成了不可水解的烷基碳酸酯类似物。对这些类似物抑制人类 sirtuin 同源物 SIRT1 的能力进行了评估。
• Alkyloxycarbonyl group migration in furanosides
  作者：Marcela Dvorakova、Marie Pribylova、Radek Pohl、Marie E. Migaud、Tomas Vanek

  DOI：10.1016/j.tet.2012.05.117

  日期：2012.8

  A migration of methyloxycarbonyl group from secondary to primary hydroxyl was observed in furanosides (ribosides and xylosides) under usual desilylation conditions using tetrabutylammonium fluoride. The migration was studied further on several alkyloxycarbonyl furanosides under either basic or acidic conditions. As follows from C-13 labelling experiments and product distribution, the migration in xylosides, proceeds intramolecularly via six-membered cyclic carbonate, whereas in ribosides, the migration is intermolecular. Acidic conditions prevented the migration in ribosides whereas the migration in xylosides was circumvented under neutral conditions. (c) 2012 Elsevier Ltd. All rights reserved.
• New Electronic Analogs of the Sialyl Cation:  N-Functionalized 4-Acetamido-2,4-dihydroxypiperidines. Inhibition of Bacterial Sialidases
  作者：Ian B. Parr、Benjamin A. Horenstein

  DOI：10.1021/jo9708497

  日期：1997.10.1
• Design and Synthesis of 5‘-Deoxy-5‘-Phenyladenophostin A, a Highly Potent IP₃ Receptor Ligand¹
  作者：Tetsuya Mochizuki、Yoshihiko Kondo、Hiroshi Abe、Colin W. Taylor、Barry V. L. Potter、Akira Matsuda、Satoshi Shuto

  DOI：10.1021/ol0602710

  日期：2006.3.1

  5'-Deoxy-5'-phenyladenophostin A (5), designed as a useful IP3 receptor ligand based on the previous structure-activity relationship studies, was successfully synthesized via two key stereoselective glycosidation steps. This compound proved to be a highly potent IP3 receptor agonist.