octyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside | 224952-98-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: octyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside
• 英文别名: (2R,3S,4R,5R)-2-octoxy-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane
• CAS: 224952-98-1
• 化学式: C₃₄H₄₄O₅
• 分子量: 532.72
• InChiKey: ZMTCPXDTJUCTSQ-YVEASBDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  39
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  octyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到octyl β-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

  摘要：

  The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl beta-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-alpha-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00260-4
• 作为产物：
  描述：

  1-O-acetyl-2,3,5-tris-O-(benzyl)-α, β-D-arabinofuranose 在 盐酸 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 1.17h， 生成 octyl 2,3,5-tri-O-benzyl-β-D-arabinofuranoside
  参考文献：
  名称：

  Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis

  摘要：

  The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl beta-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-alpha-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00260-4

文献信息

• Stereospecific Furanosylations Catalyzed by Bis-thiourea Hydrogen-Bond Donors
  作者：Andrew B. Mayfield、Jan B. Metternich、Adam H. Trotta、Eric N. Jacobsen

  DOI：10.1021/jacs.0c00335

  日期：2020.2.26

  We report a new method for stereoselective O-furanosylation reactions promoted by a precisely tailored bis-thiourea hydrogen-bond-donor catalyst. Furanosyl donors outfitted with an anomeric dialkylphosphate leaving group undergo substitution with high anomeric selectivity, providing access to the challenging 1,2-cis substitution pattern with a range of alcohol acceptors. A variety of stereochemically distinct, benzyl-protected glycosyl donors were engaged successfully as substrates. Mechanistic studies support a stereospecific mechanism in which rate-determining substitution occurs from a catalyst-donor resting-state complex.
• Acceptor-Dependent Stereoselective Glycosylation:  2‘-CB Glycoside-Mediated Direct β-<scp>d</scp>-Arabinofuranosylation and Efficient Synthesis of the Octaarabinofuranoside in Mycobacterial Cell Wall
  作者：Yong Joo Lee、Kyunghoon Lee、Eun Hye Jung、Heung Bae Jeon、Kwan Soo Kim

  DOI：10.1021/ol0510668

  日期：2005.7.1

  A reliable and generally applicable direct method for the stereoselective beta-arabinofuranosylation employing a 2'-carboxybenzyl arabinofuranoside as the glycosyl donor has been established. The acyl-protective group on glycosyl acceptors is essential for the beta-stereoselectivity. The power of the present acceptor-dependent glycosylation method was demonstrated by the efficient synthesis of the octaarabinofuranoside in arabinogalactan and lipoarabinomannan found in mycobacterial cell wall.
• Synthesis of arabinofuranosides via low-temperature activation of thioglycosides
  作者：Haifeng Yin、Todd L Lowary

  DOI：10.1016/s0040-4039(01)01133-9

  日期：2001.8

  The synthesis of oligosaccharides containing arabinofuranose residues is reported. Coupling of thioglycoside donors 4, 6, or 7 and with acceptors 8-17 using N-iodosuccinimide and silver triflate activation provided glycosides with varying degrees of stereocontrol. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of d-arabinofuranosides using propane-1,3-diyl phosphate as the anomeric leaving group
  作者：Yuan Li、Gurdial Singh

  DOI：10.1016/s0040-4039(01)01327-2

  日期：2001.9

  2',3',5'-Tri-O-benzyl-D-arbinofurano-1-O-propane-1,3-diylphosphate was activated with TMSOTf to afford 1-O-linked arabinofuranosides with good stereoselectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of oligosaccharide fragments of mannosylated lipoarabinomannan from Mycobacterium tuberculosis
  作者：Vinodhkumar Subramaniam、Todd L. Lowary

  DOI：10.1016/s0040-4020(99)00260-4

  日期：1999.5

  The synthesis of three mannosyl-arabinosides 4-6 found as terminal epitopes of mannosylated lipoarabinomannan (ManLAM) from Mycobacterium tuberculosis is reported. A key step in the synthesis of the required protected octyl beta-D-arabinofuranoside derivative 7 involved glycosylation of octanol by 5-O-acetyl-2,3-di-O-benzyl-alpha-D-arabinofuranosyl chloride (12) in the absence of a promoter. The sequential addition of the mannopyranose residues to 7, using thioglycosides 8 and 9, provided the protected oligosaccharides 17, 19, and 21. Deprotection by deacylation and then hydrogenation afforded the targets. (C) 1999 Elsevier Science Ltd. All rights reserved.