p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside | 1385090-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• 英文别名: 2-[(2S,3R,4R,5S,6R)-2-(4-chlorophenyl)sulfanyl-5-hydroxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 1385090-38-9
• 化学式: C₃₄H₃₀ClNO₆S
• 分子量: 616.134
• InChiKey: QFDJTMKIROJWSO-ITRDTHECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 以 二氯甲烷 为溶剂， 反应 35.5h， 生成 methyl 2,3-di-O-acetyl-4,6-O-benzylidene-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  A Scalable Approach to Obtaining Orthogonally Protected β-d-Idopyranosides

  摘要：

  A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging beta-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various beta-idopyranose-containing oligosaccharide targets to further probe their biological functions.

  DOI：

  10.1021/jo300764k
• 作为产物：
  描述：

  4-chlorophenyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 4.0h， 生成 p-chlorophenyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  A Scalable Approach to Obtaining Orthogonally Protected β-d-Idopyranosides

  摘要：

  A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging beta-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various beta-idopyranose-containing oligosaccharide targets to further probe their biological functions.

  DOI：

  10.1021/jo300764k

文献信息

• Regio- and stereo-controlled synthesis of 6-deoxy-β-<scp>d</scp>-<i>ido</i>-heptopyranosides related to <i>Campylobacter jejuni</i> HS:4
  作者：Saba Homayonia、Pengfei Zhang、Ping Zhang、Chang-Chun Ling

  DOI：10.1039/d3ob00683b

  日期：——

  antibodies against the CPS structures of C. jejuni HS:4 is an attractive strategy. The 6-deoxy-ido-configuration of the heptose combined with its β-anomeric configuration makes the chemical synthesis of the disaccharide very challenging. Here, we report an efficient synthesis to obtain the key repeating disaccharide and its analog in reverse order plus a trisaccharide. Our synthesis features a highly efficient

  空肠弯曲菌是一种细菌病原体，每年在全世界引起数亿例食源性胃肠炎病例。这种细菌引起的感染还与多种形式的感染后自身免疫后遗症有关，这些后遗症可能非常严重，包括危及生命的吉兰-巴利综合征。空肠弯曲菌 HS:4的荚膜多糖 (CPS)由非常独特的重复二糖单元组成，其特征是 β-1,4-连接的 6-脱氧-β- D- ido -庚吡喃糖和N-乙酰基- β- D-葡萄糖胺。引发针对空肠弯曲菌HS:4的 CPS 结构的碳水化合物特异性抗体是一种有吸引力的策略。6-脱氧-庚糖的ido构型与其 β-异头构型相结合，使得二糖的化学合成非常具有挑战性。在这里，我们报告了一种有效的合成方法，以获得关键的重复二糖及其逆序类似物加上三糖。我们的合成方法通过中间体 2,3-anHydro-β- D - talo - 高效、一步立体和区域选择性地将 β- D -半乳糖-吡喃庚糖苷转化为 6-脱氧-β- D - ido -吡喃庚糖苷。吡喃庚糖苷。
• Epoxide‐Mediated Trans‐Thioglycosylation and Application to the Synthesis of Oligosaccharides Related to the Capsular Polysaccharides of <i>C. jejuni</i> HS:4
  作者：Saba Homayonia、Chang‐Chun Ling

  DOI：10.1002/chem.202303753

  日期：2024.2.26

  used as potent immunogens in vaccinations. The regio- and stereoselective opening of pyranosyl epoxides has been taken advantage of to obtain a family of very challenging thiooligosaccharide antigens related to Campylobacter jejuni HS:4 with unprecedented efficiency.

  抗酶硫代糖苷有潜力用作疫苗接种中的有效免疫原。利用吡喃环氧化物的区域选择性和立体选择性打开，以前所未有的效率获得了与空肠弯曲杆菌HS:4 相关的一系列非常具有挑战性的硫寡糖抗原。
• A Scalable Approach to Obtaining Orthogonally Protected β-<scp>d</scp>-Idopyranosides
  作者：Rachel Hevey、Alizée Morland、Chang-Chun Ling

  DOI：10.1021/jo300764k

  日期：2012.8.17

  A practical method to obtain orthogonally protected D-idopyranose from D-galactose has been developed, which is the first method to enable synthesis of the challenging beta-D-idopyranoside linkage. The method relies on a key double inversion at O-2 and O-3 in an easily prepared D-galactose derivative, which proceeds regio- and stereoselectively through a 2,3-anhydrotalopyranoside; reaction using a selection of alkoxides affords exclusively the 3-O-alkylidopyranoside, which can be used to generate an orthogonally protected monosaccharide. The process is scalable and requires minimal purification, so it could be used to produce building blocks to aid in the synthesis of various beta-idopyranose-containing oligosaccharide targets to further probe their biological functions.