phenyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside | 402831-61-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: phenyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
• 英文别名: phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-mannopyranoside；S-phenyl-2-azido-3-O-benzyl-4,6-di-O-benzylidene thiomannoside；(2R,4aR,6R,7S,8R,8aS)-7-azido-2-phenyl-8-phenylmethoxy-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 402831-61-2
• 化学式: C₂₆H₂₅N₃O₄S
• 分子量: 475.568
• InChiKey: GYANYTDSBUXYFW-XCEYXQIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside 在 二苯基亚砜 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.42h， 生成 C₅₀H₆₆Cl₃N₇O₁₃Si
  参考文献：
  名称：

  Synthesis of Staphylococcus aureus Type 5 Trisaccharide Repeating Unit: Solving the Problem of Lactamization

  摘要：

  The chemical synthesis of an orthogonally protected trisaccharide derived from the polysaccharide of Staphylococcus aureus Type 5, which is an attractive candidate for the development of immunotherapies, is described. The challenging alpha-fucosylation and beta-mannosylation are addressed through the careful choice of protecting groups. Lactamization of a beta-D-ManpNAcA moiety during deprotection was avoided by a late stage oxidation approach. Versatility of the trisaccharide was demonstrated by its transformation into a spacer-containing repeating unit suitable for immunological investigations.

  DOI：

  10.1021/acs.orglett.5b00031
• 作为产物：
  描述：

  phenyl 2-azido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-α-D-mannopyranoside 在 potassium tert-butylate 、 sodium hydride 、 tetrafluoroboric acid dimethyl ether complex 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 phenyl 2-azido-2-deoxy-3-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  A novel approach towards the stereoselective synthesis of 2-azido-2-deoxy-β-d-mannosides

  摘要：

  Low temperature mannosylation of glycosyl acceptors under the agency of S-(4-methoxyphenyl) benzenethiosulfinate (MPBT) and trifluoromethanesulfonic anhydride (Tf2O) with p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-alpha -D-mannopyranoside, readily available from D-mannosamine hydrochloride, affords 2-azido-2-deoxy-D-mannosides with high beta -selectivity in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01880-9

文献信息

• Sulfonium Triflate Mediated Glycosidations of Aryl 2-Azido-2-deoxy-1-thio-<scp>D</scp>-mannosides
  作者：Remy E. J. N. Litjens、Leendert J. van den Bos、Jeroen D. C. Codée、Richard J. B. H. N. van den Berg、Herman S. Overkleeft、Gijsbert A. van der Marel

  DOI：10.1002/ejoc.200400784

  日期：2005.3

  (phenylsulfinyl)piperidine (BSP) 1b/ trifluoromethanesulfonic anhydride (Tf2O) and diphenyl sulfoxide (DPS) 1c/Tf2O-mediated glycosidations of 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides 2a/b is described. Application of the BSP/Tf2O activator led to productive condensations using p-methoxyphenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannoside (2b) as a donor, while the more powerful

  (苯基亚磺酰基)哌啶 (BSP) 1b/三氟甲磺酸酐 (Tf2O) 和二苯基亚砜 (DPS) 1c/Tf2O 介导的 2-azido-3-O-benzyl-4,6- 糖苷化在产率和立体选择性方面的有效性描述了 O-benzylidene-2-deoxy-D-thiomannosides 2a/b。BSP/Tf2O 活化剂的应用导致使用对甲氧基苯基 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannoside (2b) 作为供体进行生产性缩合，而更多的强大的 DPS/Tf2O 组合使用对甲氧基苯基和苯基 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-thiomannosides 2a/b 得到了相似的结果。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451
• Ph₂SO/Tf₂O:  a Powerful Promotor System in Chemoselective Glycosylations Using Thioglycosides
  作者：Jeroen D. C. Codée、Remy E. J. N. Litjens、René den Heeten、Herman S. Overkleeft、Jacques H. van Boom、Gijs A. van der Marel

  DOI：10.1021/ol034312t

  日期：2003.5.1

  [GRAPHICS]Diphenylsulfoxide in combination with triflic anhydride provides a very potent thiophilic glycosylation promotor system, capable of activating disarmed thioglycosides. The usefulness of this novel thiophilic activator is illustrated in a successful chemoselective glycosylation sequence in which the donor thioglycoside in the first condensation step may be either armed or disarmed.