methyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside | 204918-50-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside
• CAS: 204918-50-3
• 化学式: C₃₆H₃₈O₇Si
• 分子量: 610.779
• InChiKey: JOAZEAYROJJPED-UWEBUPBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  44.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 methyl 5-O-[2-O-benzoyl-3,5-O-(1,1,3,3-tetraisopropylsiloxane-1,3-diyl)-α-D-arabinofuranosyl]-2,3-di-O-benzoyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Arabinofuranosyl Oligosaccharides from Mycobacteria:  Synthesis and Effect of Glycosylation on Ring Conformation and Hydroxymethyl Group Rotamer Populations

  摘要：

  A series of alpha-D-arabinofurnnosyl oligosaccharides (2-8) that an fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequential addition of arabinofuranosyl residues from thioglycoside donors to methyl glycoside accepters. High-resolution NMR studies on the final products provided all (3)J(H,H) values, which were in turn used in PSEUROT 6.2 calculations to determine both the identity and equilibrium populations of preferred conformers for each furanose ring in these glycans. Comparison of the ring conformers present in 2-8 with these available in the parent monosaccharide, methyl alpha-D-arabinofuranose (16), allowed the determination of the effect of glycosylation upon ring conformation. At equilibrium, 16 exists as an approximately equimolar mixture of T-0(4) (North, N) and T-2(3) (South, S) conformers. These studies showed that glycosylation of 16 at OH5 resulted in no significant change in conformer identity or population relative to 16. However, glycosylation of OH3 resulted in a change in the identity of the N species (to E-O) and a significant favoring of this conformer at equilibrium. These trends were seen in all of the oligosaccharides. The populations of the three possible staggered rotamers (gg, gt, tg) about the C4-C5 bond were essentially the same for all residues in 2-8, and thus this equilibrium does not appear to be sensitive to glycosylation.

  DOI：

  10.1021/ja993543l
• 作为产物：
  描述：

  叔丁基二苯基氯硅烷 在 吡啶 作用下， 反应 4.0h， 生成 methyl 2,3-di-O-benzoyl-5-O-tert-butyldiphenylsilyl-α-D-arabinofuranoside
  参考文献：
  名称：

  Arabinofuranosyl Oligosaccharides from Mycobacteria:  Synthesis and Effect of Glycosylation on Ring Conformation and Hydroxymethyl Group Rotamer Populations

  摘要：

  A series of alpha-D-arabinofurnnosyl oligosaccharides (2-8) that an fragments of the arabinan portions of two polysaccharides present in the cell wall of Mycobacterium tuberculosis have been synthesized. Preparation of the oligosaccharides involved the sequential addition of arabinofuranosyl residues from thioglycoside donors to methyl glycoside accepters. High-resolution NMR studies on the final products provided all (3)J(H,H) values, which were in turn used in PSEUROT 6.2 calculations to determine both the identity and equilibrium populations of preferred conformers for each furanose ring in these glycans. Comparison of the ring conformers present in 2-8 with these available in the parent monosaccharide, methyl alpha-D-arabinofuranose (16), allowed the determination of the effect of glycosylation upon ring conformation. At equilibrium, 16 exists as an approximately equimolar mixture of T-0(4) (North, N) and T-2(3) (South, S) conformers. These studies showed that glycosylation of 16 at OH5 resulted in no significant change in conformer identity or population relative to 16. However, glycosylation of OH3 resulted in a change in the identity of the N species (to E-O) and a significant favoring of this conformer at equilibrium. These trends were seen in all of the oligosaccharides. The populations of the three possible staggered rotamers (gg, gt, tg) about the C4-C5 bond were essentially the same for all residues in 2-8, and thus this equilibrium does not appear to be sensitive to glycosylation.

  DOI：

  10.1021/ja993543l

文献信息

• Efficient one-pot syntheses of α-d-arabinofuranosyl tri- and tetrasaccharides present in cell wall polysaccharide of Mycobacterium tuberculosis
  作者：Xing-Yong Liang、Li-Min Deng、Xia Liu、Jin-Song Yang

  DOI：10.1016/j.tet.2009.11.038

  日期：2010.1

  Two alpha-D-arabinofuramosyl oligosaccharides (2 and 3) found as constituent parts of the polysaccharide portion from the cell wall of Mycobacterium tuberculosis have been efficiently synthesized via a one-pot glycosylation procedure in which a key step is the chemoselective activation between D-arabinofuranosyl trichloroacetimidate donor 4 and partially protected aryl thioglycosides 5 or 7, respectively. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthetic arabinofuranosyl oligosaccharides as Mycobacterial arabinosyltransferase substrates
  作者：Joseph D. Ayers、Todd L. Lowary、Caroline B. Morehouse、Gurdyal S. Besra

  DOI：10.1016/s0960-894x(98)00049-3

  日期：1998.3

  A series of arabinofuranosyl oligosaccharides found as constituent parts of the polysaccharide portion of the cell wall of Mycobacterium tuberculosis have been chemically synthesized. Screening of these oligosaccharides as substrates for arabinosyltransferases present in mycobacterial membrane preparations suggests that modified oligosaccharide analogs as small as disaccharides may be inhibitors of glycan biosynthesis. Such inhibitors would be of potential utility as lead compounds in the identification of new drugs for the treatment of mycobacterial infections. (C) 1998 Elsevier Science Ltd. All rights reserved.