methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide | 149440-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
• 英文别名: (2S,3R,4S,5R,6R)-2-(methyldisulfanyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 149440-92-6
• 化学式: C₃₅H₃₈O₅S₂
• 分子量: 602.816
• InChiKey: JAMIVFJGDYNIIP-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  96.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 3,4,6-tri-O-benzyl-2-deoxy-1-thio-D-arabino-hexono-1,5-O-lactone
  参考文献：
  名称：

  糖基硫代-O-内酯。第一部分。亲核试剂的制备和反应

  摘要：

  呋喃类和吡喃类糖基硫代-O-内酯是通过S-苯甲酰基硫代糖苷的光解或通过S-糖基硫代亚磺酸盐的热解制备的，其结果比用Lawesson试剂对糖基内酯硫磺化的效果更好。从二金呋喃呋喃糖基二硫化物7或Manofuranosyl甲基二硫化物8（流程2）获得的硫代亚磺酸盐的热解得到低产率的硫代-O-内酯2。然而，通过原位烷基化衍生自的硫醇基阴离子获得的S-苯甲酰基硫代糖苷6的光解作用。5以78–89％的优势领先至2。类似地，二硫代碳酸酯10转化，通过图11A，进入核糖-噻ø内酯12（79％）。热解的全乙酰硫代亚磺酸酯的14（方案3导致了中间硫代）O-内酯15，其后行容易β消去的AcOH（的16层析期间，75％）。将过苄基化的S-吡喃葡萄糖基二硫代碳酸酯18（方案4）转化为S-苯甲酰基硫代葡萄糖苷19或成异头甲基二硫化物21a / b的混合物。而光解19导致在适中的产率以2-脱氧硫代ø内酯20，氧化21

  DOI：

  10.1002/hlca.19930760223
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-glucopyranosyl methanethiosulfonate 在 4 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 methyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl disulfide
  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

• Glycosyldisulfides: a new class of solution and solid phase glycosyl donors
  作者：Benjamin G. Davis、Sarah J. Ward、Phillip M. Rendle

  DOI：10.1039/b008734n

  日期：——

  Mixed glycosyl disulfides are not only glycomimetics but also glycosyl donors that may be readily constructed in either armed ether-protected or disarmed ester-protected and in soluble or solid-supported forms from corresponding glycosyl methanethiosulfonates and used in the glycosylation of a variety of representative acceptors.

  混合糖基二硫化物不仅是糖模拟物，而且是糖基供体，可以很容易地以武装醚保护或解除武装酯保护的形式构建，并以相应的糖基甲硫代磺酸盐以可溶或固体支持的形式构建，并用于各种代表性受体的糖基化.
• 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,.
• Glyconothio-<i>O</i>-lactones. Part I. Preparation and reactions with nucleophiles
  作者：Marianne Hürzeler、Bruno Bernet、Andrea Vasella

  DOI：10.1002/hlca.19930760223

  日期：1993.3.24

  dithiocarbonate 24b and the disulfide 25. The ring conformations of the δ-thio-O-lactones, flattened 4C1 for 15 and 4 and B2,5 for 26, are similar to the ones of the O-analogous oxo-glyconolactones. The reaction of 2 (Scheme 5) with MeLi and then with MeI gave the thioglycoside 27 (29%) and the dimeric thio-O-lactone 29 (47%). The analogous treatment of 2 with lithium dimethylcuprate (LiCuMe2) and MeI led

  呋喃类和吡喃类糖基硫代-O-内酯是通过S-苯甲酰基硫代糖苷的光解或通过S-糖基硫代亚磺酸盐的热解制备的，其结果比用Lawesson试剂对糖基内酯硫磺化的效果更好。从二金呋喃呋喃糖基二硫化物7或Manofuranosyl甲基二硫化物8（流程2）获得的硫代亚磺酸盐的热解得到低产率的硫代-O-内酯2。然而，通过原位烷基化衍生自的硫醇基阴离子获得的S-苯甲酰基硫代糖苷6的光解作用。5以78–89％的优势领先至2。类似地，二硫代碳酸酯10转化，通过图11A，进入核糖-噻ø内酯12（79％）。热解的全乙酰硫代亚磺酸酯的14（方案3导致了中间硫代）O-内酯15，其后行容易β消去的AcOH（的16层析期间，75％）。将过苄基化的S-吡喃葡萄糖基二硫代碳酸酯18（方案4）转化为S-苯甲酰基硫代葡萄糖苷19或成异头甲基二硫化物21a / b的混合物。而光解19导致在适中的产率以2-脱氧硫代ø内酯20，氧化21