ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside | 369386-67-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2S,3R,4S,5S,6R)-2-ethylsulfanyl-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 369386-67-4
• 化学式: C₃₁H₃₆O₆S
• 分子量: 536.689
• InChiKey: CXICTCQKLDCWFA-NBCLCUQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 4 A molecular sieve 、 sodium methylate 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 5-azidopentyl (4-O-acetyl-3-O-allyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c
• 作为产物：
  描述：

  ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 lithium aluminium tetrahydride 、 三氯化铝 、 对甲苯磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.43h， 生成 ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Fragments of the Glycocalyx Glycan of the ParasiteSchistosoma mansoni

  摘要：

  The chemical synthesis of alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)-beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, beta-D-GalpNAc-(1 --> 4)-[alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2, and alpha-L-Fucp-(1 --> 3)-beta-D-GalpNAc-(1 --> 4)- [alpha-L-Fucp-(1 --> 3)-]beta-D-GlcpNAc-(1 --> 3)-alpha-D-GalpO(CH2)(5)NH2 is described. These structures represent fucosylated oligosaccharide fragments of the glycocalyx glycan of the cercarial stage of the parasite Schistosoma mansoni, and in protein-conjugated form they are potential diagnostics in the search for antibodies raised against the glycan in the serum of infected humans.

  DOI：

  10.1002/1521-3765(20020104)8:1<151::aid-chem151>3.0.co;2-c

文献信息

• ——
  作者：P. E. Cheshev、E. A. Khatuntseva、A. G. Gerbst、Yu. E. Tsvetkov、A. S. Shashkov、N. E. Nifantiev

  DOI：10.1023/a:1024905419008

  日期：——

  selectively protected derivatives of tetrasaccharide GalNAc(beta 1-->3)Gal(alpha 1-->4)Gal(beta 1-->4)Glc beta-OCH2CH2N3 and pentasaccharide Gal(beta 1-->3)GalNAc(beta 1-->3)Gal(alpha 1-->4)Gal(beta 1-->4)Glc beta-OCH2CH2N3 in 88 and 73% yields, respectively. Removal of O-protecting groups, substitution of acetyl group for N-trichloroacetyl group, and reduction of the aglycone azide group resulted in the

  6-三-O-乙酰基-2-脱氧-1-硫代-2-三氯乙酰氨基-β-D-吡喃半乳糖苷和4-三氯乙酰胺基苯基4,6-二-O-乙酰基-2-脱氧-3-O-（2，在N-碘代琥珀酰亚胺和三氟甲磺酸存在下，二氯甲烷中的3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基）-1-硫-2-三氯乙酰胺基-β-D-吡喃半乳糖苷导致相应的选择性保护四糖GalNAc（β1-> 3）Gal（α1-> 4）Gal（β1-> 4）Glcβ-OCH2CH2N3的衍生物和五糖Gal（β1-> 3）GalNAc（β1- -> 3）Gal（alpha 1-> 4）Gal（beta 1-> 4）Glc beta-OCH2CH2N3，产率分别为88％和73％。除去O-保护基，将乙酰基替换为N-三氯乙酰基，以及将糖苷配基叠氮基还原，得到目标2-氨基乙基球蛋白三-，-四-和-五糖，
• Synthesis of oligosaccharides corresponding to Streptococcus pneumoniae type 9 capsular polysaccharide structures
  作者：Mia Alpe、Stefan Oscarson

  DOI：10.1016/s0008-6215(02)00263-x

  日期：2002.10

  alpha-D-Glcp-(1-->3)-beta-D-ManpNAc-(1-->4)-beta-D-Glcp, corresponding to structures from Streptococcus pneumoniae capsular polysaccharides type 9A, L, V and type 9N, respectively, have been synthesised as 2-aminoethyl glycosides and as protected TMSE glycosides. Ethyl thioglycosides were used as glycosyl donors and NIS/TfOH (in CH(2)Cl(2) for beta-linkages) and DMTST (in Et(2)O for alpha-linkages) as promoters

  两种三糖，α-D-Galp-（1-> 3）-beta-D-ManpNAc-（1-> 4）-beta-D-Glcp和alpha-D-Glcp-（1-> 3） -β-D-ManpNAc-（1-> 4）-β-D-Glcp分别对应于肺炎链球菌荚膜多糖9A，L，V和9N型多糖的结构，已被合成为2-氨基乙基糖苷和作为受保护的TMSE糖苷。乙基硫代糖苷用作糖基供体，而NIS / TfOH（对于β键，则在CH（2）Cl（2）中）和DMTST（对于α键，则在Et（2）O中）用作糖基化促进剂。通过叠氮化置换具有β-D-葡萄糖构型的2-O-三氟甲磺酸酯，可以在二糖水平上引入β-ManNAc基序。保护基图案允许连续合成更大的结构。