methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside | 88337-87-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
• 英文别名: Methyl 3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-2,4-di-O-benzoyl-α-L-rhamnopyranoside；methyl 2,4-di-O-benzoyl-3-O-(2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside；Rha2Ac3Ac4Ac(a1-3)[Bz(-2)][Bz(-4)]a-Rha1Me；[(2S,3S,4R,5R,6R)-5-benzoyloxy-6-methoxy-2-methyl-4-[(2S,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxyoxan-3-yl] benzoate
• CAS: 88337-87-5
• 化学式: C₃₃H₃₈O₁₄
• 分子量: 658.656
• InChiKey: RHXKEXZIBSXQOD-OKDXAVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  168
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 在 甲醇 、 乙酰氯 作用下， 以95.9%的产率得到methyl α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  SYNTHESIS OF A XYLOSYLATED RHAMNOSE PENTASACCHARIDE—THE REPEATING UNIT OF THE O-SPECIFIC SIDE CHAIN OF LIPOPOLYSACCHARIDES FROM THE REFERENCE STRAINS FOR Stenotrophomonas maltophilia SEROGROUP O18

  摘要：

  A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-->3)-[beta-L-Xylp-(1-->2)-] [beta-L-Xylp-(1-->4)-]alpha-L-Rhap-(1-->3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-->3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-alpha-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).

  DOI：

  10.1081/car-120003740
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 在 4 A molecular sieve 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 methyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  苯基硒代糖苷是新型的通用糖基供体。硫糖苷的选择性活化

  摘要：

  用三氟甲磺酸银和无水碳酸钾对乙基巯基糖苷在乙基硫代糖苷上的选择性活化，可以从硒代糖苷供体和硫代糖苷受体高效合成二糖。通过添加1,1,3,3，-四甲基脲或可力丁淬灭活化。

  DOI：

  10.1016/0040-4039(91)80005-q

文献信息

• Articial carbohydrate antigens: A block synthesis of a linear, tetrasaccharide repeating-unit of the Shigella flexneri varianty polysaccharide
  作者：Hans-Peter Wessel、David R. Bundle

  DOI：10.1016/0008-6215(83)88465-1

  日期：1983.12

  beta-D-glucopyranosyl-(1----2)-alpha-L- rhamnopyranoside. Together with previously synthesized tetrasaccharides of the Shigella flexneri Y O-antigen, this oligosaccharide has been used to study the conformation of O-antigens and to assist in the selection of S. flexneri, variant Y, specific monoclonal antibodies.

  甲基2,4-二-O-苯甲酰基-α-L-鼠李吡喃糖苷与2,3,4-三-O-乙酰基-α-L-鼠李糖吡喃糖苷的糖基化反应得到甲基2,4-二-O-苯甲酰基-3 -O-（2,3,4-三-O-乙酰基-α-L-鼠李吡喃糖基）-α-L-鼠李糖吡喃糖苷（4），产率为93％。用二溴甲基甲基醚将4转化成相应的糖基溴化物。在Koenigs-Knorr条件下，该溴化物与8-（甲氧羰基）辛基2-O-（2-乙酰氨基-4,6-O-亚苄基-2-脱氧-β-D-甘露糖基）-3,4-二-反应O-苄基-α-L-鼠李吡喃糖苷，以91％的产率提供被保护的四糖。去除保护基团得到8-（甲氧基羰基）辛基O-α-L-鼠李吡喃糖基-（1 ---- 3）-O-α-L-鼠李吡喃糖基-（1 ---- 3）-O-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基-（1 ---- 2）-α-L-鼠李糖吡喃糖苷。
• The in situ activation of thioglycosides with bromine: an improved glycosylation method
  作者：Jan O. Kihlberg、David A. Leigh、David R. Bundle

  DOI：10.1021/jo00296a055

  日期：1990.4
• Synthesis of ligands related to the O-specific antigen of type 1 Shigella dysenteriae. 3. Glycosylation of 4,6-O-substituted derivatives of methyl 2-acetamido-2-deoxy-.alpha.-D-glucopyranoside with glycosyl donors derived from mono- and oligosaccharides.
  作者：Pavol Kovac、Kevin J. Edgar

  DOI：10.1021/jo00034a047

  日期：1992.4

  Methyl O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranoside, obtained by silver trifluoromethanesulfonate-mediated condensation of methyl 2,4-di-O-benzoyl-alpha-L-rhamnopyranoside and 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl bromide (3), was cleaved with dichloromethyl methyl ether (DCMME) to give O-(2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl)-(1 --> 3)-2,4-di-O-benzoyl-alpha-L-rhamnopyranosyl chloride (9). Condensations of 1,3,4,6-tetra-O-acetyl-alpha-D-galactopyranose with 3 and 9, followed by treatment of the products with DCMME yielded, respectively, glycosyl chlorides 12 and 17. Each of these, as well as 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl chloride was condensed with 4,6-O-substituted (benzylidene, tetraisopropyl-disiloxane-1,3-diyl, or benzyl) derivatives of methyl 2-acetamido-2-deoxy-alpha-D-glucopyranoside, using CH2Cl2, ether, or a mixture thereof as the solvent. The formation of the desired alpha-D-galactopyranosyl linkage was favored when ether was the solvent. Under these conditions, however, the combined yield of the condensation products decreased, especially when less reactive synthons were used. The alpha-linked products obtained were deprotected to give the methyl alpha-glycosides of the tetra, tri-, and the disaccharide related to the chemical repeating unit of the O-specific side chain of the lipopolysaccharide of Shigella dysenteriae type 1. Synthesis of methyl alpha-glycosides of three other constituents of the same polymeric antigen [alpha-L-Rha-(1 --> 3)-alpha-L-Rha, alpha-L-Rha-(1 --> 2)-alpha-D-Gal, and alpha-L-Rha-(1 --> 3)-alpha-L-Rha-(1 --> 2)-alpha-D-Gal] are also described.
• KIHLBERG, JAN O.;LEIGH, DAVID A.;BUNDLE, DAVID R., J. ORG. CHEM., 55,(1990) N, C. 2860-2863
  作者：KIHLBERG, JAN O.、LEIGH, DAVID A.、BUNDLE, DAVID R.

  DOI：——

  日期：——