methyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranoside | 153223-25-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranoside
• 英文别名: (6aS,8R,9R,9aR)-8-methoxy-2,2,4,4-tetra(propan-2-yl)-6a,8,9,9a-tetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-9-ol
• CAS: 153223-25-7
• 化学式: C₁₈H₃₈O₆Si₂
• 分子量: 406.667
• InChiKey: WSCLYCQPYILECV-XWTMOSNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranoside 在 重铬酸吡啶 、 3 A molecular sieve 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以98%的产率得到methyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-threo-pentofuranosid-2-ulose
  参考文献：
  名称：

  Batch, Alexandre; Czernecki, Stanislas, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 935 - 940

  摘要：

  DOI：
• 作为产物：
  描述：

  L-(+)-arabinose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 methyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-α-L-arabinofuranoside
  参考文献：
  名称：

  Batch, Alexandre; Czernecki, Stanislas, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 935 - 940

  摘要：

  DOI：

文献信息

• Stereoselective synthesis of Arabidopsis CLAVATA3 (CLV3) glycopeptide, unique protein post-translational modifications of secreted peptide hormone in plant
  作者：Sophon Kaeothip、Akihiro Ishiwata、Yukishige Ito

  DOI：10.1039/c3ob41212a

  日期：——

  The unique hydroxylproline (Hyp)-linked O-glycan modification is a common process in hydroxyproline-rich glycoproteins (HRGPs). The modification occurs through post-translational hydroxylation at 4-position of proline residues some of which are followed by O-glycosylation at the resulting Hyp which is also found in some secreted peptide hormones such as CLAVATA3 (CLV3) of Arabidopsis thaliana plants. An active mature CLV3 is a tridecapeptide linked to β-L-Araf-(1→2)-β-L-Araf-(1→2)-β-L-Araf at a Hyp residue in the center of the peptide sequence such as Arg-Thr-Val-Hyp-Ser-Gly-Hyp(L-Arafn)-Asp-Pro-Leu-His-His-His (n = 3). We report here the synthesis of the secreted and modified CLV3 glycopeptide with all glycoforms (Araf0–3CLV3) of A. thaliana plants. A highly stereoselective β-arabinofuranosylation of Hyp derivatives as the key step of the synthesis of CLV3 glycopeptide was achieved by NAP ether-mediated IAD, which was effectively applied to the synthesis of oligoarabinosylated hydroxylproline [Hyp(L-Araf1–3)] derivatives. Fmoc-solid phase peptide synthesis was carried out using COMU as the coupling reagent for the introduction of [Hyp(L-Araf0–3)] derivatives as well as further elongation to the CLV3 glycopeptides.

  独特的羟脯氨酸(Hyp)连接的O-糖基化修饰是羟脯氨酸富集糖蛋白(HRGPs)中的常见过程。这种修饰通过在脯氨酸残基的4位进行翻译后羟基化发生，其中一些随后在生成的Hyp上发生O-糖基化，这在一些分泌的肽类激素中也存在，例如拟南芥植物中的CLAVATA3 (CLV3)。成熟的活性CLV3是一个十三肽，与β-L-Araf-(1→2)-β-L-Araf-(1→2)-β-L-Araf在肽序列中心的Hyp残基连接，例如Arg-Thr-Val-Hyp-Ser-Gly-Hyp(L-Arafn)-Asp-Pro-Leu-His-His-His (n = 3)。我们在这里报告了合成所有糖型(Araf0–3CLV3)的拟南芥植物分泌和修饰的CLV3糖肽。通过NAP醚介导的IAD实现了对Hyp衍生物的高度立体选择性β-阿拉伯呋喃糖基化，这是合成CLV3糖肽的关键步骤，并有效地应用于合成寡阿拉伯糖基化羟脯氨酸[Hyp(L-Araf1–3)]衍生物。使用COMU作为偶联试剂，通过Fmoc固相肽合成引入了[Hyp(L-Araf0–3)]衍生物，并进一步延伸至CLV3糖肽。
• Regio- and stereoselective syntheses of l-pentose derivatives from l-arabinose
  作者：Grigorii G. Sivets

  DOI：10.1016/j.tet.2017.12.045

  日期：2018.3

  were accomplished via simple and efficient reduction of methyl 2-O-mesyl-l-arabinofuranoside with L-Selectride or tandem reaction involving a complex hydride 2-deoxygenation/acylation of intermediate 2-deoxysugar. A new synthesis of 2′-deoxy-2′-fluoro-β-l-arabinofuranosyl thymine (l-FMAU) was performed using a mild fluorination of protected l-ribofuranoside and a novel sequence of conversions for

  新颖升-arabinose，升-核糖，2-脱氧-1-核糖和2-氟-2-脱氧升-arabinose衍生物由易于获得的合成升-arabinose。通过1,2-二-O-的区域选择性转化，研究了不同的合成途径，将甲基3,5-二-O-酰化-1-阿拉伯糖（呋喃核糖）呋喃糖苷作为有价值的中间体，用于制备C-2官能化的1-戊糖。乙酰-3,5-二-O-新戊酰-1-呋喃呋喃糖和甲基l的选择性酰化-阿拉伯呋喃糖苷与4-氯苯甲酰或新戊酰氯。甲基2-脱氧-α- 1-核糖呋喃糖苷，其3,5-二-O-酰基衍生物，制备抗病毒2'-脱氧-1-核苷的宝贵前体的简短的三步五步合成法是通过简单的方法完成的和高效率还原的2- ö -mesyl- 1-阿拉伯呋喃糖苷与三仲丁基硼氢化锂或涉及中间体2-脱氧糖的复合氢化物2-脱氧/酰化串联反应。2'-脱氧-2'-氟-β - 1-阿拉伯呋喃糖基胸腺嘧啶（1- FMAU）的新合成是使用受保护
• [5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates - A Novel Type of Nucleotide Analogs Related to HPMPA. I. Derivatives with L-arabino, D-arabino, 2-Deoxy-L-erythro and 2-Deoxy-L-threo Configuration
  作者：Miroslav Otmar、Ivan Rosenberg、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc19932159

  日期：——

  [5-(Adenin-9-yl)-5-deoxypentofuranosyl]phosphonates, a new type of nucleotide analogs with fixed HPMPA structure, have been prepared. The synthesis of compounds of L-arabino (IIa, IIb), D-arabino(XIVa, XIVb), 2-deoxy-L-erythro(IIIa, IIIb) and 2-deoxy-L-threo(IVa, IVb) configuration is based on the Michelis-Arbuzov reaction of the fully protected methyl glycosides with triethyl phosphite and trimethylsilyl triflate which leads to anomeric mixture of diethyl (L-pentofuranosyl) phosphonates. The protected 5-O-tosyl derivatives react with sodium salt of adenine to give N⁹-substituted products which after total deprotection afforded the tittle nucleotide analogs. The fixation of the partial structure of HPMPA to form five-membered ring leads to a significant decrease, or a total loss, of biological activity.

  已经制备了一种新型核苷酸类似物，即[5-(腺嘌呤-9-基)-5-脱氧戊糖基]磷酸酯，其具有固定的HPMPA结构。L-阿拉伯 (IIa, IIb)、D-阿拉伯 (XIVa, XIVb)、2-脱氧-L-赤 (IIIa, IIIb) 和2-脱氧-L-顺 (IVa, IVb) 配置的化合物的合成基于全保护甲基糖苷与三乙基磷酸酯和三甲基硅基三氟甲烷的Michelis-Arbuzov反应，导致二乙酰（L-戊糖基）磷酸酯的异构混合物。保护的5-O-甲苯磺酰衍生物与腺嘌呤的钠盐反应，得到N⁹-取代产物，经过全去保护后得到所需的核苷酸类似物。将HPMPA的部分结构固定形成五元环，导致生物活性显著降低或完全丧失。
• The core trisaccharide of α-l-arabinofuranan: synthesis of methyl 3,5-di-O-α-l-arabinofuranosyl-α-l-arabinofuranoside
  作者：Satoshi Kaneko、Yasuyuki Kawabata、Tadashi Ishii、Yasuo Gama、Isao Kusakabe

  DOI：10.1016/0008-6215(94)00327-c

  日期：1995.3
• Batch, Alexandre; Czernecki, Stanislas, Journal of Carbohydrate Chemistry, 1994, vol. 13, # 6, p. 935 - 940
  作者：Batch, Alexandre、Czernecki, Stanislas

  DOI：——

  日期：——