O-α-D-Galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-D-ribitol | 131328-71-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-Galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-D-ribitol
• 英文别名: α-Galp-(1-3)-α-Glcp-(1-3)-α-Rhap-(1-4)-RibOH；O-(α-D-galactopyranosyl)-(1->3)-O-(α-D-glucopyranosyl)-(1->3)-O-(α-L-rhamnopyranosyl)-(1->4)-D/L-ribitol；alpha-D-Galp-(1->3)-alpha-D-Glcp-(1->3)-alpha-L-Rhap-(1->4)-D-ribitol；(2S,3S,4R)-4-[(2S,3R,4R,5S,6S)-4-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-methyloxan-2-yl]oxypentane-1,2,3,5-tetrol
• CAS: 131328-71-7
• 化学式: C₂₃H₄₂O₁₉
• 分子量: 622.575
• InChiKey: LRYSZFIZZGTHGY-XSDHNAQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -7.3
• 重原子数：
  42
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  318
• 氢给体数：
  13
• 氢受体数：
  19

反应信息

• 作为产物：
  描述：

  2,3,5-Tri-O-benzyl-4-O-<2,4-di-O-acetyl-3-O-<2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranosyl>-α-L-rhamnopyranosyl>-D-ribitol 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、392.24 kPa 条件下， 生成 O-α-D-Galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->3)-O-α-L-rhamnopyranosyl-(1->4)-D-ribitol
  参考文献：
  名称：

  肺炎链球菌6A和6B型荚膜多糖结构成分的合成

  摘要：

  O-alpha-d-Glucopyranosyl-（1 ---- 3）-alpha，beta-L-鼠李吡喃糖（15），O-alpha-D-吡喃半乳糖基-（1 ---- 3）-O-alpha-D -吡喃葡萄糖基-（1 ---- 3）-α-α，β-L-鼠李糖吡喃糖（17），O-α-D-吡喃吡喃糖基-（1 ---- 3）-O-α-D-吡喃葡糖基-（ 1 ---- 3）-O-α-L-鼠李吡喃糖基-（1 ---- 3）-D-核糖醇（23）和O-α-D-半乳糖吡喃糖基-（1 ---- 3）- O-α-D-吡喃葡萄糖基-（1 ---- 3）-O-α-L-鼠李糖基吡喃糖基-（1 ---- 4）-D-核糖醇（27），它们是荚膜多糖的结构成分肺炎链球菌6A和6B型（[---- 2] -alpha-D-Galp-（1 ---- 3）-alpha-D-Glcp-（1 ---- 3）-alpha-L-Rhap -已经合成了-（1

  DOI：

  10.1016/0008-6215(90)84051-u

文献信息

• Isolation and structural studies of phosphate-containing oligosaccharides from alkaline and acid hydrolysates of Streptococcus pneumoniae type 6B capsular polysaccharide
  作者：Jan E.G. van Dam、Jan Breg、Ronald Komen、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/0008-6215(89)80008-4

  日期：1989.4

  The capsular polysaccharide of Streptococcus pneumoniae serotype 6B [----2)-alpha-D-Galp-(1----3)-alpha-D-Glcp-(1----3)-alpha-L-Rhap-( 1----4)- D-RibOH-(5-P----]n was depolymerised under alkaline (NaOH) and acidic (HF) conditions. The former treatment yielded, as the major component, alpha-2-P-Galp-(1----3)-alpha-Glcp-(1----3)-alpha-Rhap-(1----4)-5- P-RibOH. The latter treatment at -16 degrees gave

  肺炎链球菌血清型6B [---- 2）-alpha-D-Galp-（1 ---- 3）-alpha-D-Glcp-（1 ---- 3）-alpha-L- Rhap-（1 ---- 4）-D-RibOH-（5-P ----] n在碱性（NaOH）和酸性（HF）条件下解聚，前一种处理产生的主要成分为α -2-P-Galp-（1 ---- 3）-alpha-Glcp-（1 ---- 3）-alpha-Rhap-（1 ---- 4）-5-P-RibOH。在-16度下处理得到alpha-Galp-（1 ---- 3）-alpha-Glcp-（1 ---- 3）-alpha-Rhap-（1 ---- 4）-Rib OH-（5 -P ---- 2）-alpha-Galp-（1 ---- 3）-alpha-Glcp-（1 ---- 3）-alpha-Rhap-（1 ---- 4）-Rib OH并在4度下得到alpha-Galp-（1
• Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages
  作者：Archana R. Parameswar、Papapida Pornsuriyasak、Nicole A. Lubanowski、Alexei V. Demchenko

  DOI：10.1016/j.tet.2007.07.036

  日期：2007.10

  The synthesis of the repeating units of pneumococcal polysaccharide serotypes 6A and 6B and derivatives thereof is described. Application of S-benzoxazolyl and S-thiazolinyl glycosides allowed rapid oligosaccharide assembly and provided complete stereoselectivity in challenging 1,2-cis glucosylations and galactosylations. The oligosaccharide assembly was accomplished in an efficient manner by selective activation of thioimidoyl leaving groups over thioglycosides. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B
  作者：Ted M. Slaghek、Anita H. van Oijen、Augustinus A.M. Maas、Johannis P. Kamerling、Johannes F.G. Vliegenthart

  DOI：10.1016/0008-6215(90)84051-u

  日期：1990.10

  copyranosyl-(1----3)- O-alpha-L-rhamnopyranosyl-(1----4)-D-ribitol (27), which are structural elements of the capsular polysaccharides of Streptococcus pneumoniae types 6A and 6B ([----2)-alpha-D-Galp-(1----3)-alpha-D-Glcp-(1----3)-alpha-L-Rhap- (1----X)- D-Rib-ol-(5-P----]n; 6A X = 3, 6B X = 4), have been synthesised. Ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside (3) was coupled

  O-alpha-d-Glucopyranosyl-（1 ---- 3）-alpha，beta-L-鼠李吡喃糖（15），O-alpha-D-吡喃半乳糖基-（1 ---- 3）-O-alpha-D -吡喃葡萄糖基-（1 ---- 3）-α-α，β-L-鼠李糖吡喃糖（17），O-α-D-吡喃吡喃糖基-（1 ---- 3）-O-α-D-吡喃葡糖基-（ 1 ---- 3）-O-α-L-鼠李吡喃糖基-（1 ---- 3）-D-核糖醇（23）和O-α-D-半乳糖吡喃糖基-（1 ---- 3）- O-α-D-吡喃葡萄糖基-（1 ---- 3）-O-α-L-鼠李糖基吡喃糖基-（1 ---- 4）-D-核糖醇（27），它们是荚膜多糖的结构成分肺炎链球菌6A和6B型（[---- 2] -alpha-D-Galp-（1 ---- 3）-alpha-D-Glcp-（1 ---- 3）-alpha-L-Rhap -已经合成了-（1