methyl 2,3,4,6-tetra-O-benzyl-1-thio-b-glucopyranoside | 173395-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-benzyl-1-thio-b-glucopyranoside
• 英文别名: (3R,4S,5R,6R)-2-methylsulfanyl-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 173395-56-7
• 化学式: C₃₅H₃₈O₅S
• 分子量: 570.75
• InChiKey: UILNWDYGLDOQAD-BMURFIBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  41
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-benzyl-1-thio-b-glucopyranoside 在 四氯化碳 、 Oxone 、 氢氧化钾 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 生成 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol
  参考文献：
  名称：

  A Ramberg-Bäcklund approach to exo-glycals

  摘要：

  A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01822-x
• 作为产物：
  描述：

  甲基 2,3,4,6-O-四苄基-alpha-D-吡喃葡萄糖苷 在 三丁基膦 、 硫酸 、 三氟化硼乙醚 作用下， 以 水 、 溶剂黄146 为溶剂， 生成 methyl 2,3,4,6-tetra-O-benzyl-1-thio-b-glucopyranoside
  参考文献：
  名称：

  A Ramberg-Bäcklund approach to exo-glycals

  摘要：

  A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01822-x

文献信息

• Indium(III) Triflate: A Highly Efficient Catalyst for Reactions of Sugars^[1]
  作者：Santosh Kumar Giri、Monika Verma、K. P. Ravindranathan Kartha

  DOI：10.1080/07328300802458970

  日期：2008.12.11

  Indium(III) trifluoromethanesulfonate has been found to be extremely efficient in catalyzing acyl transfer reactions of various carbohydrates and their derivatives. Selective acetolyses of certain benzyl ethers/isopropylidene acetals of sugars have been possible using In(OTf)3 in Ac2O (neat). Reaction of the per-O-acetate of 2-deoxy-2-phthalimido-D-glucose with benzyl mercaptan in the presence of In(OTf)3

  已经发现三氟甲磺酸铟（III）在催化各种碳水化合物及其衍生物的酰基转移反应中非常有效。使用In（OTf）3在Ac2O中（纯净）可以对某些糖的苄基醚/异亚丙基缩醛进行选择性乙酰水解。在In（OTf）3存在下2-脱氧-2-邻苯二甲酰亚胺基-D-葡萄糖的全-O-乙酸酯与苄硫醇的反应导致高产率地形成相应的硫代糖苷。在In（OTf）3的存在下，也非常有效地实现了各种碳水化合物的异亚丙基和亚苄基缩醛的轻松形成和水解。结果表明，In（OTf）3在合成碳水化合物化学中具有广阔的前景。
• Activation and synthetic applications of thiostannanes. A new method for synthesis of thio- and selenoglycosides
  作者：Tsuneo Sato、Yukihiro Fujita、Junzo Otera、Hitosi Nozaki

  DOI：10.1016/0040-4039(92)88060-i

  日期：1992.1

  Exposure of thiostannane to acetyl or methyl glycosides in the presence of a catalytic amount of Bu2Sn(OTf)2 provides thioglycosides in good yields. Selenoglycosidation is achieved in a like manner by use of selenostannane.

  在催化量的Bu 2 Sn（OTf）2的存在下将硫代锡烷暴露于乙酰基或甲基糖苷可提供高收率的硫代糖苷。通过使用硒炔诺酮以类似的方式实现硒代糖苷化。
• A Ramberg-Bäcklund approach to exo-glycals
  作者：Frank K. Griffin、Paul V. Murphy、Duncan E. Paterson、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(98)01822-x

  日期：1998.10

  A new route to exo-glycals is described which starts from S-glycoside dioxides and utilises Meyers' variant of the Ramberg-Backlund rearrangement. The methodology is successful with glucose, galactose, mannose, xylose, fucose and ribose derivatives, and has been used to prepare di-, tri- and tetra-substituted alkenes. (C) 1998 Elsevier Science Ltd. All rights reserved.