3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol | 219864-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol
• 英文别名: trimethyl-[2-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]ethynyl]silane
• CAS: 219864-01-4
• 化学式: C₃₉H₄₄O₅Si
• 分子量: 620.861
• InChiKey: XOXSQZSZQDXZOO-INMKTMPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  45
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol
  参考文献：
  名称：

  X-Ray Crystal Structure Determinations of Galactosylacetylene Building Blocks

  摘要：

  We report the crystal structures of two galactosylacetylenes: 3,7-anhydro-4,5,6,8-tetra- O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mann ooctitol (7) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol (8). A short overview of the synthetic chemistry used to obtain these targets is mentioned.

  DOI：

  10.1080/07328303.2011.554935
• 作为产物：
  描述：

  4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-galactooct-3-ulopyranose 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以73%的产率得到3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mannooctitol
  参考文献：
  名称：

  X-Ray Crystal Structure Determinations of Galactosylacetylene Building Blocks

  摘要：

  We report the crystal structures of two galactosylacetylenes: 3,7-anhydro-4,5,6,8-tetra- O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mann ooctitol (7) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol (8). A short overview of the synthetic chemistry used to obtain these targets is mentioned.

  DOI：

  10.1080/07328303.2011.554935

文献信息

• Potent divalent inhibitors with rigid glucose click spacers for Pseudomonas aeruginosa lectin LecA
  作者：Francesca Pertici、Roland J. Pieters

  DOI：10.1039/c2cc30234a

  日期：——

  The synthesis of a new rigid spacer based on carbohydrate-triazole repeating units and their incorporation into divalent systems is described. Inhibition studies showed that a well-matched system with a rigid spacer with flexible ends leads to the most potent inhibition of Pseudomonas aeruginosa lectin LecA.

  描述了基于碳水化合物-三唑重复单元的新型刚性间隔基的合成及其掺入二价系统的过程。抑制研究表明，带有刚性末端和柔性末端的匹配系统可最有效地抑制铜绿假单胞菌凝集素LecA。
• Novel Type of Rigid C-Linked Glycosylacetylene−Phenylalanine Building Blocks for Combinatorial Synthesis of C-linked Glycopeptides
  作者：Todd Lowary、Morten Meldal、Arnim Helmboldt、Andrea Vasella、Klaus Bock

  DOI：10.1021/jo980517h

  日期：1998.12.1

  C-linked 3- and 4-(glycosylacetylene)-Fmoc-phenylalanines were synthesized as rigid building blocks for synthesis of libraries of neoglycopeptide templates. Perbenzylated 1,5-galactonolactone, 1,5-gluconolactone, and 1,5-mannonolactone were reacted with cerium TMS-acetylide and the products reduced to the C-glycosylacetylene-TMS derivatives. The gluco and galacto configurations yielded exclusively the beta-C-glycoside, whereas the mannonolactone gave a mixture of alpha-C- and beta-C-anomer. The products were subjected to acetolysis and TMS cleavage. The resulting peracetylated glycosylacetylenes were cross-coupled with the (R,S)-N-alpha-acetyl-3- and 4-iodophenylalanine O-methyl esters by Pd(0) catalysis in piperidine to give the eight possible C-linked glycosyl amino acid building blocks 33-40 as diastereomeric pairs. These were O-deacetylated. As an example of further conversion into neoglycopeptide templates the N-acetyl group of the 4-linked galacto-diastereomeric pair 43 was hydrolyzed selectively by acylase 1 and separated from the (R)stereoisomer. The product was converted to 4-(beta-C-galactosylacetylene)(N-alpha-Fmoc-)-L-phenylalanine (52) by reaction with Fmoc-OSu. Acid hydrolysis of galactosyl acetylene phenyl alanine 43 at elevated temperature afforded the conversion of the acetylene to the 1'-oxo derivative which was also N-alpha-Fmoc protected. The building blocks were used in the glycopeptide synthesis of three neoglycopeptide templates 54, 55, and 56 known to bind to murine MHC class II E-k and to present the glycan for interaction with the T-cell receptor. This template has previously been employed to elicit a carbohydrate specific T-cell response.
• X-Ray Crystal Structure Determinations of Galactosylacetylene Building Blocks
  作者：David J. Leaver、Andrew B. Hughes、Anastasios Polyzos、Jonathan M. White

  DOI：10.1080/07328303.2011.554935

  日期：2010.11.1

  We report the crystal structures of two galactosylacetylenes: 3,7-anhydro-4,5,6,8-tetra- O-benzyl-1,1,2,2-tetradehydro-1,2-dideoxy-1-C-(trimethylsilyl)-D-glycero-L-mann ooctitol (7) and 3,7-anhydro-4,5,6,8-tetra-O-benzyl-1,1,2,2-tetradehydro-1,2-D-glycero-L-mannooctitol (8). A short overview of the synthetic chemistry used to obtain these targets is mentioned.