N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-threonine methyl ester | 77942-96-2

• 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: N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-threonine methyl ester
• 英文别名: methyl (2S,3R)-2-(phenylmethoxycarbonylamino)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxybutanoate
• CAS: 77942-96-2
• 化学式: C₄₇H₅₁NO₁₀
• 分子量: 789.923
• InChiKey: MFWHIWZDGLHSQN-WWVPIXTISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.56
• 重原子数：
  58.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  120.01
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为产物：
  描述：

  1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 在 silicon tetrafluoride 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-threonine methyl ester
  参考文献：
  名称：

  Glycosylation using glucopyranosyl fluorides and silicon-based catalysts. Solvent dependency of the stereoselection

  摘要：

  DOI：

  10.1016/s0040-4039(01)80163-5

文献信息

• Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
  作者：Chun‐Wei Chang、Chia‐Hui Wu、Mei‐Huei Lin、Pin‐Hsuan Liao、Chun‐Chi Chang、Hsiao‐Han Chuang、Su‐Ching Lin、Sarah Lam、Ved Prakash Verma、Chao‐Ping Hsu、Cheng‐Chung Wang

  DOI：10.1002/anie.201906297

  日期：2019.11.18

  Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates:

  尽管数十年来进行了大量的努力，但立体控制的化学糖基化仍然是一个主要挑战，到目前为止，仍然主要依靠反复试验。现在表明，硫糖苷的相对反应性值（RRV）是根据四种受体揭示立体选择性的指标。机理研究表明，该反应由两种不同的中间体控制：糖基三氟甲磺酸酯和来自N-卤代琥珀酰亚胺（NXS）/ TfOH的糖基卤化物。糖基卤化物的形成与α-糖苷的产生高度相关。这些发现使得能够通过使用RRV作为α/β-选择性指示剂来预见糖基化反应，并且为立体控制糖基化开发了指导方针和规则。
• Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups
  作者：Hariprasad Vankayalapati、Gurdial Singh、Isabelle Tranoy

  DOI：10.1016/s0957-4166(01)00227-0

  日期：2001.6

  Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-d-glucopyranose to diphenylphosphinic and propane-1,3-diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence

  通过添加2,3,4,6-四-O-苄基-α，β-d-吡喃葡萄糖的异头羟基可以轻松制备具有二苯基次膦酸酯和丙烷1,3-二苯基磷酸酯离去基团的糖基供体生成二苯基次膦酸和丙烷1，，3-二基二氧基磷酰氯。在三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）存在下，这些糖基供体被许多伯和仲氧亲核试剂选择性糖基化。磷酸1，3-二烷基酯的使用导致β- O-连接的糖苷的立体选择性形成。
• Stereoselective O-glycosylation reactions employing diphenylphosphinate and propane-1,3-diyl phosphate as anomeric leaving groups
  作者：Vankayalapati Hariprasad、Gurdial Singh、Isabelle Tranoy

  DOI：10.1039/a805206i

  日期：——

  Glycosidation of tetra-O-benzyl-D-glucose using diphenylphosphinate as the leaving group afforded β-O-linked glycosides as the major products, whilst the use of propane-1,3-diyl phosphate as the leaving group resulted in the exclusive formation of β-O-linked glycoside.

  使用二苯基膦酸盐作为离去基团对四-O-苄基-D-葡萄糖进行糖苷化反应，主要产物为β-O-连接糖苷，而使用丙烷-1,3-二基磷酸酯作为离去基团则只生成了β-O-连接糖苷。
• An extremely mild and general method for the stereocontrolled construction of 1,2-cis-glycosidic linkages via S-glycopyranosyl phosphorodiamidimidothioates
  作者：Hashimoto Shun-ichi、Honda Takeshi、Ikegami Shiro

  DOI：10.1016/s0040-4039(00)97729-3

  日期：——
• 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：——