3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranose

• 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: 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranose
• 英文别名: (2S,3R,4R,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-sulfanyloxan-3-ol
• 化学式: C₂₇H₃₀O₅S
• 分子量: 466.598
• InChiKey: NYHKCNLOXNUYJY-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 Oxone 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 18.0h， 生成 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranose
  参考文献：
  名称：

  方便合成 1,3-dithiolane-2-thiones：环状三硫代碳酸酯作为构象锁

  摘要：

  一系列新的 1,3-dithiolane-2-thiones 或环状三硫代碳酸酯已通过一种新的简单程序制备：用市售的乙基黄原酸钾 KSC(S)OEt 处理相应的环氧化物。产物的立体化学由 H NMR 确定，在某些情况下由单晶 X 射线数据确定。基于环己烷的 1,3dithiolane-2-thiones 揭示了碳环和杂环的转化。从单取代的环己烯氧化物获得的产物证明了取代基的轴向位置。因此，环氧化物转化为三硫代碳酸酯可用作锁定不稳定构象的环状化合物的方法。

  DOI：

  10.3998/ark.5550190.p008.671

文献信息

• PROCESS FOR PRODUCING 1,2-TRANS-GLYCOSIDE COMPOUND
  申请人：Otsuka Chemical Co., Ltd.

  公开号：EP1849794A1

  公开（公告）日：2007-10-31

  In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the process comprising using a furanose compound wherein the hydroxyl at the 2-position may have a substituent protected with a group A, or a pyranose compound which may have a substituent wherein R2 and R3 are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R2 and R3 are combined to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms, or may have intervening phenylene), and m and n are each an integer of 0 or 1.

  在从(a)呋喃糖化合物或吡喃糖化合物和(b)醇化合物制备苷化合物时，制备苷键相对于 C-2 羟基选择性地反式定位的苷化合物的工艺，该工艺包括使用呋喃糖化合物，其中 2 位的羟基可能具有被 A 基团保护的取代基，或使用吡喃糖化合物，其中可能具有取代基 其中R2和R3相同或不同，各自为具有1至4个碳原子的烷基或具有或不具有取代基的芳基，或R2和R3结合形成具有2至4个碳原子的亚烷基(该亚烷基可被具有1至4个碳原子的烷基取代，或可有中间的亚苯基)，m和n各自为0或1的整数。
• Synthesis of Glycosylthiols and Reactivity Studies
  作者：Ravindra T. Dere、Amit Kumar、Vipin Kumar、Xiangming Zhu、Richard R. Schmidt

  DOI：10.1021/jo200624e

  日期：2011.9.16

  The acid-catalyzed reaction of 1,2-anhydro-3,4,6-tri-O-benzyl-alpha-D-glucopyranose (7) as glycosyl donor with bis-trimethylsilyl sulfide as acceptor affords the alpha-thiol. Hence, this sterically hindered S-nucleophile as acceptor should provide with O-glycosyl trichloroacetimidates as glycosyl donors that have nonparticipating groups at C-2, glycosylthiols with the thiol group in axial position. This was confirmed for various donors (4, 16-19) with the exception of the corresponding mannosyl donor (20). However, powerful participating groups at C-2 of the donor (23-28) governed the anomeric selectivity.
• Process for Producing 1,2-Trans-Glycoside Compound
  申请人：Yamago Shigeru

  公开号：US20080177049A1

  公开（公告）日：2008-07-24

  In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the process comprising using a furanose compound wherein the hydroxyl at the 2-position may have a substituent protected with a group A, or a pyranose compound which may have a substituent wherein R 2 and R 3 are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R 2 and R 3 are combined to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms, or may have intervening phenylene), and m and n are each an integer of 0 or 1.
• US8212013B2
  申请人：——

  公开号：US8212013B2

  公开（公告）日：2012-07-03
• US8664372B2
  申请人：——

  公开号：US8664372B2

  公开（公告）日：2014-03-04