ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside | 143838-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,4aR,6S,7R,8S,8aS)-7-benzoyloxy-6-ethylsulfanyl-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 143838-81-7
• 化学式: C₂₉H₂₈O₇S
• 分子量: 520.603
• InChiKey: ZRMRTIABQQKBAN-SWJKKVKRSA-N

物化性质

• 沸点：
  656.8±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside 在 吡啶 、 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 sodium methylate 、 sodium hydride 、 DMTST 、 三氟乙酸 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 乙二醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (R)-glycidyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line

  摘要：

  Synthesis of three galactoglycerolipids (3-O-(beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00473-8
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 吡啶 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 2.5h， 生成 ethyl 2,3-di-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of galactoglycerolipids found in the HT29 human colon carcinoma cell line

  摘要：

  Synthesis of three galactoglycerolipids (3-O-(beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-2-O-palmitoyl-sn-glycerol, 3-O-(alpha-D-galactopyranosyl-(1-->4)-beta-D-galactopyranosyl)-1-O-hexadecyl-sn-glycerol), and the corresponding glycerolipid (1-O-hexadecyl-2-O-palmitoyl-sn-glycerol) is described. The first two compounds were recently identified in the human colon carcinoma cell line HT29. The three-carbon synthon (S)-glycidol was used for construction of the glycerol moiety. Glycosylation of (S)-glycidol with protected galactosyl and digalactosyl donors produced galactosyl and digalactosyl glycidols. Lewis acid catalyzed opening of the epoxide produced protected galactosyl and digalactosyl glycerolipids. Deprotection, or palmitoylation followed by deprotection, yielded the target compounds. The corresponding glycerolipid was synthesized analogously and an oxidation-reduction procedure for tritiation was developed. The synthesized compounds will be used in studies of the role of galactosyl glycerolipids in differentiation and colon cancer development. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00473-8

文献信息

• Discovery of Oligosaccharide Antigens for Semi‐Synthetic Glycoconjugate Vaccine Leads against <i>Streptococcus suis</i> Serotypes 2, 3, 9 and 14**
  作者：Shuo Zhang、Mauro Sella、Julinton Sianturi、Patricia Priegue、Dacheng Shen、Peter H. Seeberger

  DOI：10.1002/anie.202103990

  日期：2021.6.21

  Streptococcus suis bacteria are one of the most serious health problems for pigs and an emerging zoonotic agent in humans working in the swine industry. S. suis bacteria express capsular polysaccharides (CPS) a major bacterial virulence factor that define the serotypes. Oligosaccharides resembling the CPS of S. suis serotypes 2, 3, 9, and 14 have been synthesized, glycans related to serotypes 2 and

  猪链球菌是猪最严重的健康问题之一，也是养猪业人类中新出现的人畜共患病病原体。猪链球菌表达荚膜多糖（CPS），这是定义血清型的主要细菌毒力因子。类似于猪链球菌血清型 2、3、9 和 14 的 CPS 的寡糖已被合成，与血清型 2 和 9 相关的聚糖被放置在聚糖阵列表面上以筛选来自受感染猪的血液。以这种方式鉴定了用于开发半合成猪链球菌血清型 2 和 9 糖复合兽用疫苗的先导抗原。
• The presence of water improves reductive openings of benzylidene acetals with trimethylaminoborane and aluminium chloride
  作者：Andrei A. Sherman、Yuri V. Mironov、Olga N. Yudina、Nikolay E. Nifantiev

  DOI：10.1016/s0008-6215(03)00015-6

  日期：2003.4

  efficient for the reductive openings of the cyclic benzylidene acetals with Me(3)N x BH(3) in tetrahydrofurane than the AlCl(3) alone. Under proposed conditions, the dioxane-type 4,6-O-bezylidene acetals of hexopyranosides give regioselectively the corresponding 4-hydroxy,6-O-benzyl derivatives in excellent yields. Reductive openings of the dioxolane-type 3,4-O-benzylidene acetals of galactopyranoside are

  由无水AlCl（3）和H（2）O以3：1比例原位形成的酸性试剂比四氢呋喃中Me（3）N x BH（3）还原环亚苄基乙缩醛的效率高得多单独的AlCl（3）。在提出的条件下，己吡喃糖苷的二恶烷型4，6-O-亚苄基乙缩醛以优异的产率选择性地给出相应的4-羟基，6-O-苄基衍生物。半乳糖吡喃糖苷的二氧戊环型3,4-O-亚苄基乙缩醛的还原开口也非常有效且具有区域选择性，可生成3-O-苄基衍生物（来自3,4-O-外亚苄基乙缩醛）或4-O-苄基衍生物（来自3,4-O-内-亚苄基缩醛）取决于缩醛碳原子的构型。
• 1,3-Dibromo-5,5-dimethylhydantoin as promoter for glycosylations using thioglycosides
  作者：Fei-Fei Xu、Claney L Pereira、Peter H Seeberger

  DOI：10.3762/bjoc.13.195

  日期：——

  1,3-Dibromo-5,5-dimethylhydantoin (DBDMH), an inexpensive, non-toxic and stable reagent, is a competent activator of thioglycosides for glycosidic bond formation. Excellent yields were obtained when triflic acid (TfOH) or trimethylsilyl trifluoromethanesulfonate (TMSOTf) were employed as co-promoters in solution or automated glycan assembly on solid phase.

  1,3-二溴-5,5-二甲基乙内酰脲（DBDMH）是一种廉价，无毒且稳定的试剂，是硫糖苷用于糖苷键形成的有效活化剂。当三氟甲磺酸（TfOH）或三氟甲磺酸三甲基甲硅烷基酯（TMSOTf）在溶液中或固相上自动聚糖组装中用作助促进剂时，可获得优异的收率。
• Chemical and chemoenzymatic syntheses of sialyl Lewisa tetrasaccharide antigen
  作者：Yuanyuan Jiang、Shichao Duan、Jiaming Li、Yanli Zhao、Jinsong Yang

  DOI：10.1039/d4ob00809j

  日期：——

  Sialyl Lewisa (sLea), also known as cancer antigen 19-9, is a tumor-associated carbohydrate antigen. In this article, chemical and chemoenzymatic syntheses of a tetrasaccharide glycan 1 structurally derived from sLea are reported. Challenges involved in the chemical synthesis include the highly stereoselective construction of 1,2-cis-α-L-fucoside and α-D-sialoside, as well as the assembly of the 3

  Sialyl Lewis a (sLe a )，也称为癌抗原 19-9，是一种肿瘤相关碳水化合物抗原。在这篇文章中，报道了结构上源自 sLe a的四糖聚糖1的化学和化学酶合成。化学合成中涉及的挑战包括1,2-顺式-α- L-岩藻糖苷和α -D-唾液酸苷的高度立体选择性构建，以及3,4-二取代的N-乙酰葡糖胺亚基的组装。全苄化硫代岩藻糖苷和N-乙酰基-5- N ,4- O-恶唑烷酮保护的唾液酸硫代糖苷分别作为糖基供体，有效制备了所需的α-岩藻糖苷和α-唾液酸苷。 3,4-支链葡糖胺主链通过3- O然后4- O糖基化序列建立，其中葡糖胺部分的3-羟基首先被糖基化，然后是4-羟基。还利用了一种简便的化学酶方法来合成目标分子。化学获得的游离二糖30以酶催化的区域和立体特异性方式依次唾液酸化和岩藻糖基化，以高产率形成1 。附加的接头1可以共价连接至载体蛋白以用于进一步的免疫学研究。
• Garegg, Per J.; Kvarnstroem, Ingemar; Niklasson, Annika, Journal of Carbohydrate Chemistry, 1993, vol. 12, # 7, p. 933 - 954
  作者：Garegg, Per J.、Kvarnstroem, Ingemar、Niklasson, Annika、Niklasson, Gunilla、Svensson, Stefan C. T.

  DOI：——

  日期：——