phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside | 158716-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside
• 英文别名: phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside；phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-α-D-thiomannopyranoside
• CAS: 158716-10-0
• 化学式: C₂₈H₂₈O₆S
• 分子量: 492.593
• InChiKey: MLSHZMQGZCMAKM-BNNSEFEDSA-N

物化性质

• 沸点：
  624.4±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside 在 10% palladium on active carbon N-碘代丁二酰亚胺 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 三乙胺 为溶剂， -50.0~20.0 ℃ 、101.33 kPa 条件下， 反应 121.15h， 生成 methyl α-D-glucopyranosyl-(1->3)-α-D-mannopyranosyl-(1->2)-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894
• 作为产物：
  描述：

  phenyl 4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 在 四丁基碘化铵 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 吡啶 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.0h， 生成 phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894

文献信息

• Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
  作者：Sibin Wang、Oleksii Zhelavskyi、Jeonghyo Lee、Alonso J. Argüelles、Yaroslav Ya. Khomutnyk、Enoch Mensah、Hao Guo、Rami Hourani、Paul M. Zimmerman、Pavel Nagorny

  DOI：10.1021/jacs.1c08448

  日期：2021.11.10

  differentially protected mono- and disaccharide derivatives. To further demonstrate the utility of the polymeric catalysts, the same batch of (R)-Ad-TRIP-PS catalyst was recycled and reused to accomplish single-pot gram-scale syntheses of 6 differentially protected d-glucose derivatives. The subsequent exploration of the reaction mechanism using NMR studies of deuterated and nondeuterated substrates revealed

  本文介绍了使用手性磷酸 (CPA) 及其固定化聚合物变体 ( R )-Ad-TRIP-PS 和 ( S )-SPINOL-PS 作为催化剂对单糖二醇进行区域选择性缩醛保护的研究。这些催化剂控制的区域选择性缩醛化反应对各种d-葡萄糖-、 d-半乳糖-、 d-甘露糖-和l-岩藻糖衍生的 1,2-二醇具有高区域选择性（高达 >25:1 rr）并且可以根据手性催化剂的选择以区域发散的方式进行。聚合物催化剂可以方便地回收并多次重复使用，用于克级官能化，催化负载量低至 0.1 mol%，并且它们的性能通常优于其单体变体的性能。这些区域选择性 CPA 催化的缩醛化与常见的羟基官能化成功地结合为单锅套叠程序，产生了 32 种区域异构纯的差异保护的单糖和二糖衍生物。为了进一步证明聚合物催化剂的实用性，同一批的( R )-Ad-TRIP-PS催化剂被回收并重复使用，以完成6种差异保护的d-葡萄糖衍生物的单锅克
• Sonication-Assisted Oligomannoside Synthesis
  作者：Christabel T. Tanifum、Cheng-Wei T. Chang

  DOI：10.1021/jo8019835

  日期：2009.1.16

  We have investigated the use of sonication for the synthesis of oligomannosides. A convenient sonication-mediated glycosylation protocol that is applicable to traditional glycosylation methods has been developed. This protocol can be applicable for activating glycosyl donors that are known to have low reactivity which enable the synthesis of oligomannosides of particular biological interest with the same efficiency.
• Synthesis of some partially substituted methyl α-d- and phenyl 1-thio-α-d-mannopyranosides for the preparation of manno-oligosaccharides
  作者：Zoltán Szurmai、Lajos Balatoni、András Lipták

  DOI：10.1016/0008-6215(94)84264-7

  日期：1994.2
• Highly Stereoselective Synthesis of α-<scp>d</scp>-Mannopyranosyl Phosphosugars
  作者：David Crich、Sébastien Picard

  DOI：10.1021/jo902254w

  日期：2009.12.18

  alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.
• Influence of the O3 Protecting Group on Stereoselectivity in the Preparation of <i>C</i>-Mannopyranosides with 4,6-<i>O</i>-Benzylidene Protected Donors
  作者：David Crich、Indrajeet Sharma

  DOI：10.1021/jo101453y

  日期：2010.12.17

  alpha-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.