ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside | 289057-14-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-4-[tert-butyl(dimethyl)silyl]oxy-6-[(2R,3S,4S,5R,6R)-2-ethylsulfanyl-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-3,5-bis(phenylmethoxy)oxan-2-yl]methyl 2-chloroacetate
• CAS: 289057-14-3
• 化学式: C₅₇H₇₁ClO₁₁SSi
• 分子量: 1027.79
• InChiKey: GDLANHPZPRPRCO-OKKOVQOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.31
• 重原子数：
  71.0
• 可旋转键数：
  25.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  109.37
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 26.0h， 以71%的产率得到ethyl 2,4-di-O-benzyl-6-O-chloroacetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of the Leishmania LPG Core Heptasaccharyl myo-Inositol

  摘要：

  Total synthesis of the core heptasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)[Glcp(alpha1-PO4-6)Manp](alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, and the corresponding hexasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)Manp(alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, found in the lipophosphoglycans of Leishmania parasites are described. The target molecules contain synthetic challenges such as an unusual internal galactofuranosyl residue and an anomeric phosphodiester. The synthesis was accomplished using a convergent block synthetic strategy. Four building blocks, a trigalactoside, a dimannoside, a glucosyl inositolphosphate, and a glucosyl-alpha -1-H-phosphonate, all appropriately protected, were used. The trigalactoside was linked to the dimannoside followed by glycosylation with the glucosyl inositolphosphate to produce the fully protected hexasaccharyl myo-inositol. Subsequent oxidative coupling of the glucosyl-H-phosphonate formed the anomeric phosphodiester linkage to produce the protected heptasaccharyl myo-inositol. Both the assembly order of the subunits and sequence of deprotection were essential for the successful synthesis of these complex molecules. The deprotection was accomplished by deacetylation and clevage of benzyl ethers with sodium in liquid ammonia, followed by acidic deacetalization/desilylation to produce the target molecules.

  DOI：

  10.1021/ja001515t
• 作为产物：
  描述：

  ((2R,3R,4S,5S,6R)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-ethylsulfanyl-tetrahydro-pyran-4-yloxy)-tert-butyl-dimethyl-silane 在 2,3,5-三甲基吡啶 、 4 A molecular sieve 、 三氟化硼乙醚 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 1.83h， 生成 ethyl (2,4-di-O-benzyl-3-O-t-butyldimethylsilyl-6-O-chloroacetyl-1-thio-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  肌醇Phosphoglycan片段的合成中发现利什曼原虫寄生虫

  摘要：

  的合成1和图2a是使用块合成策略描述。化合物4被用作两个甘露糖衍生物的前体，这两个甘露糖衍生物耦合在一起，形成了双甘露糖苷结构单元。硫代糖苷7与8偶联生成肌醇磷酸聚糖9a，将其选择性脱保护并与2,3,4,6-四-O-苄基-α-d-吡喃葡萄糖-1-基H-膦酸酯反应形成受保护的靶分子12。通过酸性脱缩醛/去甲硅烷基化作用对12进行脱保护并随后进行催化氢解反应，导致端基异构磷酸二酯裂解生成1。在液体氨中用钠脱苄基，然后进行酸性脱缩醛/去甲硅烷基化，得到目标化合物2a。

  DOI：

  10.1016/s0040-4020(00)00239-8