p-tolyl N-benzyl-2-amino-2,3-N,O-carbonyl-4,6-O-dibenzyl-2-deoxy-1-thio-β-D-glucopyranoside | 1038395-33-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl N-benzyl-2-amino-2,3-N,O-carbonyl-4,6-O-dibenzyl-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: p-tolyl N-benzyl-2-amino-4,6-di-O-benzyl-2,3-N,O-carbonyl-2-deoxy-1-thio-β-D-glucopyranoside；(3aR,4S,6R,7S,7aR)-3-benzyl-4-(4-methylphenyl)sulfanyl-7-phenylmethoxy-6-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-pyrano[3,4-d][1,3]oxazol-2-one
• CAS: 1038395-33-3
• 化学式: C₃₅H₃₅NO₅S
• 分子量: 581.733
• InChiKey: SWHDJBPIHGKOFW-NEPHXMAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl N-benzyl-2-amino-2,3-N,O-carbonyl-4,6-O-dibenzyl-2-deoxy-1-thio-β-D-glucopyranoside 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以75%的产率得到p-tolyl N-benzyl-2-amino-4,6-di-O-benzyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine

  摘要：

  Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.021
• 作为产物：
  描述：

  溴甲苯 、 p-methylphenyl 2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-1-thio-β-D-glucopyranoside 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到p-tolyl N-benzyl-2-amino-2,3-N,O-carbonyl-4,6-O-dibenzyl-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  基于预激活方案的恶唑烷酮保护的2-氨基-2-脱氧-d-葡萄糖供体糖基化的立体选择性研究

  摘要：

  制备了各种2，3-恶唑烷酮保护的2-氨基-2-脱氧-d-葡萄糖硫代糖苷，并在添加糖基受体之前通过BSM / Tf 2 O预活化方​​案在低温下作为糖基供体进行了研究。研究了一系列糖基化的立体化学结果。由于恶唑烷酮供体中的不同保护基，导致偶联反应的立体选择性不同。4,6-二-O-苄基-N-苄基-恶唑烷酮保护的硫糖苷供体1c进行了糖基化，具有一般的β-异头异构体选择性，并且立体选择性也可能受到糖基化条件的影响。

  DOI：

  10.1016/j.tet.2008.03.103

文献信息

• Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation
  作者：Toshiki Nokami、Akito Shibuya、Yoshihiro Saigusa、Shino Manabe、Yukishige Ito、Jun-ichi Yoshida

  DOI：10.3762/bjoc.8.52

  日期：——

  Glycosyl triflates with a 2,3-oxazolidinone protecting group were generated from thioglycosides by low-temperature electrochemical oxidation. The glycosyl triflates reacted with alcohols to give the corresponding glycosides β-selectively at low temperatures. However, α-selectivity was observed in the absence of base at elevated reaction temperatures. In situ generated triflic acid promotes the isomerization of β-products to α-products.

  用低温电化学氧化从硫代糖苷生成带有2,3-噁唑啉醇保护基的糖基三氟甲磺酸酯。糖基三氟甲磺酸酯与醇在低温下反应，选择性地形成相应的糖苷β-选择性产物。然而，在高温反应条件下，在无碱存在的情况下观察到α-选择性。原位生成的三氟甲磺酸促进β-产物向α-产物的异构化。
• Joined use of oxazolidinone and desymmetric amino protection: a new strategy for protection of glucosamine
  作者：Shih-Che Lin、Chin-Sheng Chao、Chiu-Ching Chang、Kwok-Kong T. Mong

  DOI：10.1016/j.tetlet.2010.02.021

  日期：2010.4

  Joined use of N-benzyl oxazolidinone and N-benzyl-N-benzyloxycarbonyl (N-BnCbz) desymmetric amino-protecting function is reported. The new synthetic approach enables the facile preparation of type I and type 2 LacNAc disaccharides in satisfactory yields. One-pot deprotection of N-BnCbz and O-benzyl ether is achieved by hydrogenolysis under mild conditions. (C) 2010 Elsevier Ltd. All rights reserved.
• Stereoselectivity investigation on glycosylation of oxazolidinone protected 2-amino-2-deoxy-d-glucose donors based on pre-activation protocol
  作者：Yiqun Geng、Li-He Zhang、Xin-Shan Ye

  DOI：10.1016/j.tet.2008.03.103

  日期：2008.5

  Diverse 2,3-oxazolidinone protected 2-amino-2-deoxy-d-glucose thioglycosides were prepared and studied as glycosyl donors at low temperature by BSM/Tf2O pre-activation protocol before the addition of glycosyl acceptors. The stereochemistry outcomes of a series of glycosylations were investigated. Different stereoselectivities of the coupling reactions were obtained, arising from the different protecting

  制备了各种2，3-恶唑烷酮保护的2-氨基-2-脱氧-d-葡萄糖硫代糖苷，并在添加糖基受体之前通过BSM / Tf 2 O预活化方​​案在低温下作为糖基供体进行了研究。研究了一系列糖基化的立体化学结果。由于恶唑烷酮供体中的不同保护基，导致偶联反应的立体选择性不同。4,6-二-O-苄基-N-苄基-恶唑烷酮保护的硫糖苷供体1c进行了糖基化，具有一般的β-异头异构体选择性，并且立体选择性也可能受到糖基化条件的影响。