3,4-di-O-benzoyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose | 224622-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-di-O-benzoyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose
• 英文别名: [(3aR,5S,6S,7R,7aR)-7-benzoyloxy-2-methoxy-2,5-dimethyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] benzoate
• CAS: 224622-39-3
• 化学式: C₂₃H₂₄O₈
• 分子量: 428.439
• InChiKey: LHFYCZKOKCAHFO-SJFDYEJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose 在 mercury dibromide 作用下， 以 硝基甲烷 为溶剂， 以90%的产率得到methyl 2-O-acetyl-3,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Synthesis of the principal chain of the 0-antigenic polysaccharides ofShigella flexneri Communication 1. Synthesis of 2,4- and 3,4-di-o-benzoyl-?-L-rhamnopyranosides by a combination of selective acylation and deacetylation, and the synthesis of 1,2-di-o-acetyl-3,4-di-o-benzoyl-L-rhamnopyranose via 1,2-o-benzylidene-3,4-di-o-benzoyl-?-L-rhamnopyranose

  摘要：

  DOI：

  10.1007/bf01142795
• 作为产物：
  描述：

  3,4-di-O-acetyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 3,4-di-O-benzoyl-1,2-O-methoxyethylidene-β-L-rhamnopyranose
  参考文献：
  名称：

  Facile Synthesis of a Branched Trisaccharide–The Repeating Unit of Antigen O2 Polymer using Orthoester Formation - Rearrangement Strategy

  摘要：

  The synthesis of a branched trisaccharide, the repeating unit of the antigen O2 polymer containing L-rhamnose, D-mannose, and L-xylose, was achieved using orthoester formation- rearrangement strategy.

  DOI：

  10.1080/07328309908543994

文献信息

• A highly efficient and convergent synthesis of a hexasaccharide, a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1016/s0008-6215(99)00004-x

  日期：1999.1

  A highly efficient and convergent synthesis of a hexasaccharide, which is a dimer of the repeating unit of the antigen O2 polysaccharide of Stenotrophomonas maltophilia, was achieved via coupling of 2,3,4-tri-O-acetyl-alpha-L-xylopyranosyl bromide with the tetrasaccharide, allyl 4-O-3-O-[4-O-(3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-benzoyl-alpha-L-rhamnopranosyl}-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (18) by the Koenigs-Knorr method followed by deacylation. Compound 18 was readily prepared from the coupling of the disaccharide trichloroacetimidate, 4-O-(2-O-acetyl-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate (8) with the disaccharide acceptor, allyl 4-O-(2-O-acetyl-4-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside (16), and both 8 and 16 were prepared via the trichloroacetimidate method from simple starting materials. The sole use of acyl protecting groups substantially simplified protection and deprotection, and the allyl group at the reducing end of allyl 4-O-2-O[2,3,4-tri-O-acetyl-beta-L-xylopyranosyl]-3-O-[4-O-(2-O-(2,3,4-tri-O-acetyl-beta-L-rhamnopyranosyl)-3,4-di-O-benzoyl-alpha-L-rhamnopyranosyl)-2,3,6-tri-O-benzoyl-alpha-D-mannopyranosyl]-4-O-benzoyl-alpha-L-rhamnopyranosyl} -2,3,6-tri-O-benzoyl-alpha-D-mannopyranoside 19 allowed further chemical transformation. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Facile Synthesis of a Branched Trisaccharide–The Repeating Unit of Antigen O2 Polymer using Orthoester Formation - Rearrangement Strategy
  作者：Wei Wang、Fanzuo Kong

  DOI：10.1080/07328309908543994

  日期：1999.1.1

  The synthesis of a branched trisaccharide, the repeating unit of the antigen O2 polymer containing L-rhamnose, D-mannose, and L-xylose, was achieved using orthoester formation- rearrangement strategy.
• Synthesis of the principal chain of the 0-antigenic polysaccharides ofShigella flexneri Communication 1. Synthesis of 2,4- and 3,4-di-o-benzoyl-?-L-rhamnopyranosides by a combination of selective acylation and deacetylation, and the synthesis of 1,2-di-o-acetyl-3,4-di-o-benzoyl-L-rhamnopyranose via 1,2-o-benzylidene-3,4-di-o-benzoyl-?-L-rhamnopyranose
  作者：N. �. Bairamova、L. V. Bakinovskii、N. K. Kochetkov

  DOI：10.1007/bf01142795

  日期：1985.5
• Synthesis of an l-rhamnose tetrasaccharide, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci
  作者：Jianjun Zhang、Yuliang Zhu、Fanzuo Kong

  DOI：10.1016/s0008-6215(01)00258-0

  日期：2001.11

  A tetrasaccharide, alpha -L-Rhap-(1 -->3)-alpha -L-Rhap-(1 -->2)-alpha -L-Rhap-(1 --> 2)-L-Rhap, the common and major structure of the repeating unit of the O-antigenic polysaccharide of a strain of Klebsiella pneumoniae and Pseudomonas holci was synthesized as its methyl and octyl glycosides. Selective 3-O-glycosylation of allyl alpha -L-rhamnopyranoside with 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl trichloroacetimidate gave allyl 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-alpha -L-rhamnopyranoside (3). Benzoylation, deallylation, and trichloroacetimidation afforded 2,3,4-tri-O-acetyl-alpha -L-rhamnopyranosyl-(1 --> 3)-2,4-di-O-benzoyl-alpha -L-rhamnopyranosyl trichloroacetimidate (6). Self condensation of 3,4-di-O-benzoyl-beta -L-rhamnopyranose 1,2-methyl orthoester or 1,2-octyl orthoester gave methyl or octyl 2-O-acetyl-3,4-di-O-benzoyl-alpha -L-rhamnopyranosyl-(1 -->2)-3,4-di-O-benzOyl-alpha -L-rhamnopyranoside (16 or 17), and subsequent selective deacetylation gave the disaccharide acceptor (18 or 19). Coupling of 6 with 18 (or 19), followed by deacylation in ammonia-saturated methanol, produced the target tetrasacharide. (C) 2001 Elsevier Science Ltd. All rights reserved.