ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine | 77870-92-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine
• 英文别名: N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine methyl ester；methyl N-(benzyloxykarbonyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serinate；O-(2,3,4,6-O-benzyl)-α-D-galactopyranosyl-N-benzyloxycarbonyl-L-serine methyl ester；methyl (2S)-2-(phenylmethoxycarbonylamino)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 77870-92-9
• 化学式: C₄₆H₄₉NO₁₀
• 分子量: 775.896
• InChiKey: CDZSXCDCDDJFRH-WZOOWZRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 以95%的产率得到methyl 3-O-α-D-galactopyranosyl-L-serinate
  参考文献：
  名称：

  Gd3 +与各种糖肽结合方式的13C-Nmr光谱研究。

  摘要：

  使用自然丰度13C-nmr光谱研究Gd3 +与单-O-糖基化L-丝氨酸和由Gly和L-Thr组成的三肽的结合方式。当氨基酸的氨基和羧基没有被封闭时，观察到Gd3 +与它们的强相互作用；对于一些相关的，非糖基化的肽，这也是显而易见的。当氨基酸的氨基和羧基被封闭时，Gd3 +与含α-D-Galp的糖肽的糖苷氧原子（O-3）和O-2'以及与O-3和N-的显着相互作用观察到含有α-D-GalpNAc的糖肽的2'。与糖基的O-4'和O-6'弱相互作用也是可能的。尽管氨基酸受到保护，但这些金属离子与碳水化合物的相互作用仍可能在一定程度上被介导，

  DOI：

  10.1016/0008-6215(83)88387-6
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactopyranosyl methanethiosulfonate 在 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 ester methylique de la N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-L-serine
  参考文献：
  名称：

  Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration

  摘要：

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.

  DOI：

  10.1021/jo051374j

文献信息

• Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate
  作者：Mei-Yuan Hsu、Sarah Lam、Chia-Hui Wu、Mei-Huei Lin、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3390/molecules25051103

  日期：——

  dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

  描述了在微波辐射下由三氟甲磺酸二苯基铵催化的碳水化合物半缩醛的直接脱水糖基化的方法。武装和解除武装的糖基-C1-半缩醛供体均以中等至优异的产率有效糖基化，无需任何干燥剂和化学计量添加剂。该方法已成功应用于固相糖基化。
• Lacombe, J. M.; Pavia A. A.; Rocheville, J. M., Canadian Journal of Chemistry, 1981, vol. 59, p. 473 - 481
  作者：Lacombe, J. M.、Pavia A. A.、Rocheville, J. M.

  DOI：——

  日期：——
• Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration
  作者：Elizabeth J. Grayson、Sarah J. Ward、Alison L. Hall、Phillip M. Rendle、David P. Gamblin、Andrei S. Batsanov、Benjamin G. Davis

  DOI：10.1021/jo051374j

  日期：2005.11.1

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.
• 13C-n.m.r.-spectral study of the mode of binding of Gd3+ to various glycopeptides
  作者：Kilian Dill、Marsha E. Daman、Ron L. Batstone-Cunningham、Jean M. Lacombe、André A. Pavia

  DOI：10.1016/0008-6215(83)88387-6

  日期：1983.11

  Natural-abundance, 13C-n.m.r. spectroscopy was used to study the mode of binding of Gd3+ to mono-O-glycosylated L-serine and tripeptides variously composed of Gly and L-Thr. When the amino and carboxyl groups of the amino acid are not blocked, strong interaction of Gd3+ with them is observed; this is also readily apparent with some related, nonglycosylated peptides. When the amino and carboxyl groups

  使用自然丰度13C-nmr光谱研究Gd3 +与单-O-糖基化L-丝氨酸和由Gly和L-Thr组成的三肽的结合方式。当氨基酸的氨基和羧基没有被封闭时，观察到Gd3 +与它们的强相互作用；对于一些相关的，非糖基化的肽，这也是显而易见的。当氨基酸的氨基和羧基被封闭时，Gd3 +与含α-D-Galp的糖肽的糖苷氧原子（O-3）和O-2'以及与O-3和N-的显着相互作用观察到含有α-D-GalpNAc的糖肽的2'。与糖基的O-4'和O-6'弱相互作用也是可能的。尽管氨基酸受到保护，但这些金属离子与碳水化合物的相互作用仍可能在一定程度上被介导，