methyl 2,4-di-O-benzyl-3-O-(3,5-di-O-benzyl-3-C-vinyl-α-L-xylofuranosyl)-α-L-rhamnopyranoside | 1012859-21-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4-di-O-benzyl-3-O-(3,5-di-O-benzyl-3-C-vinyl-α-L-xylofuranosyl)-α-L-rhamnopyranoside
• 英文别名: (2R,3S,4S,5S)-4-ethenyl-2-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-ol
• CAS: 1012859-21-0
• 化学式: C₄₂H₄₈O₉
• 分子量: 696.838
• InChiKey: AXKYMTXXBXMJRN-QHFOTFMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  51
• 可旋转键数：
  17
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  methyl 2,4-di-O-benzyl-3-O-(3,5-di-O-benzyl-3-C-vinyl-α-L-erythro-pentofuranosyl-2-ulose)-α-L-rhamnopyranoside 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以80%的产率得到methyl 2,4-di-O-benzyl-3-O-(3,5-di-O-benzyl-3-C-vinyl-α-L-xylofuranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Indirect approach to C-3 branched 1,2-cis-glycofuranosides: synthesis of aceric acid glycoside analogues

  摘要：

  Aceric acid (3-C-carboxy-5-deoxy-alpha-L-xylofuranose) residues are present in pectic polysaccharide rhamnogalacturonan II (RG II) in the form of synthetically challenging 1,2-cis-glycofuranosides. To access synthetic fragments of RG 11 incorporating aceric acid, a four-step procedure based on C-2 epimerisation of initially prepared 1,2-trans-glycofuranoside was developed. Readily available derivatives of branched-chain L-lyxofuranose bearing a 3-C-vinyl group as a masked 3-C-carboxyl group were investigated as potential precursors of aceric acid units. In the first step of the procedure, installation of a participating group at C-2 of the furanose ring ensured stereocontrol of the O-glycosylation, which was carried out with the thioglycoside of 2-O-acetyl-3,5-di-O-benzyl-3-C-vinyl-L-lyxofuranose. After the glycosylation step, the 2-O-acetyl group was removed, the free 2-OH group was oxidised and the resulting ketone was finally reduced to form the C-3-vinyl-L-xylofuranoside. The use of L-Selectride in the key reduction reaction was essential to achieve the required stereoselectivity to generate 1,2-cis-furanoside. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.10.035

文献信息

• Indirect approach to C-3 branched 1,2-cis-glycofuranosides: synthesis of aceric acid glycoside analogues
  作者：Marcelo T. de Oliveira、David L. Hughes、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1016/j.carres.2007.10.035

  日期：2008.2

  Aceric acid (3-C-carboxy-5-deoxy-alpha-L-xylofuranose) residues are present in pectic polysaccharide rhamnogalacturonan II (RG II) in the form of synthetically challenging 1,2-cis-glycofuranosides. To access synthetic fragments of RG 11 incorporating aceric acid, a four-step procedure based on C-2 epimerisation of initially prepared 1,2-trans-glycofuranoside was developed. Readily available derivatives of branched-chain L-lyxofuranose bearing a 3-C-vinyl group as a masked 3-C-carboxyl group were investigated as potential precursors of aceric acid units. In the first step of the procedure, installation of a participating group at C-2 of the furanose ring ensured stereocontrol of the O-glycosylation, which was carried out with the thioglycoside of 2-O-acetyl-3,5-di-O-benzyl-3-C-vinyl-L-lyxofuranose. After the glycosylation step, the 2-O-acetyl group was removed, the free 2-OH group was oxidised and the resulting ketone was finally reduced to form the C-3-vinyl-L-xylofuranoside. The use of L-Selectride in the key reduction reaction was essential to achieve the required stereoselectivity to generate 1,2-cis-furanoside. (c) 2007 Elsevier Ltd. All rights reserved.