2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate | 93173-26-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate
• 英文别名: (2S,3R,4S,5R,6R)-2-isothiocyanato-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 93173-26-3
• 化学式: C₃₅H₃₅NO₅S
• 分子量: 581.733
• InChiKey: BMGXVGKYTCAXKD-KJQSSVQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl isothiocyanate 在 palladium hydroxide - carbon 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 20.5h， 生成 (3aR,4R,5S,6S,6aS)-4-(羟基甲基)-2-[[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氨基]-3a,5,6,6a-四氢环戊烯并[d][1,3]恶唑-4,5,6-三醇
  参考文献：
  名称：

  Syntheses and absolute configurations of trehazolin and its aglycon

  摘要：

  DOI：

  10.1021/ja00051a051
• 作为产物：
  描述：

  氯 2,3,4,6-四-O-苄基-|á-D-吡喃葡萄糖苷 在 四丁基溴化铵 4 A molecular sieve 、 potassium thioacyanate 作用下， 以 乙腈 为溶剂， 以12%的产率得到2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl isothiocyanate
  参考文献：
  名称：

  A New Procedure for the Synthesis of Glycosyl Isothiocyanates

  摘要：

  DOI：

  10.1055/s-1984-30885

文献信息

• Synthesis of 6-epi-trehazolin from d-ribonolactone: Evidence for the non-existence of a 5,6-ringfused structural isomer of 6-epi-trehazolin
  作者：Masao Shiozaki、Yoshiyuki Kobayashi、Masami Arai、Hideyuki Haruyama

  DOI：10.1016/s0040-4039(00)75990-9

  日期：1994.1

  6-Epi-trehazolin was synthesized in a stereocontrolled manner, and this synthesis provided proof for the non-existence of oxazine structural isomer of 6-epi-trehazolin.

  以立体控制的方式合成了6- Epi- trehazolin，该合成为6- epi- trehazolin的恶嗪结构异构体不存在提供了证据。
• Total Synthesis of Trehalase Inhibitor, Trehazolin
  作者：Seiichiro Ogawa、Chikara Uchida

  DOI：10.1246/cl.1993.173

  日期：1993.1

  The total synthesis of trehalase inhibitor, trehazolin has been accomplished by coupling the optically active aminocyclopentanepentaol with α-d-glucopyranosylisothiocyanate derivative, followed by subsequent oxazoline-ring formation and removal of the protecting groups, thereby confirming its absolute configuration.

  通过将具有光学活性的氨基环戊醇与α-d-吡喃葡萄糖基异硫氰酸酯衍生物偶联，随后形成噁唑啉环并去除保护基团，完成了三卤甲烷酶抑制剂三唑啉的全合成，从而确认了其绝对构型。
• Total Synthesis and Trehalase-Inhibitory Activity of Trehalostatin and Its Diastereoisomer
  作者：Chikara Uchida、Tatsuya Yamagishi、Seiichiro Ogawa

  DOI：10.1246/cl.1993.971

  日期：1993.6

  Complete synthesis of both diastereoisomeric structures, initially proposed for the trehalase inhibitor trehalostatin, and their biological assay have been carried out. The synthetic compounds were found to lack an inhibitory activity against trehalase, suggesting that the inhibitor would possess convincingly its 4′-epimeric structure later assigned for trehazolin.

  最初为海藻糖酶抑制剂海藻抑素提出的两种非对映异构体结构的完全合成及其生物测定已经进行。发现合成化合物缺乏对海藻糖酶的抑制活性，这表明该抑制剂具有令人信服的 4'-差向异构结构，后来被指定为海藻唑啉。
• Synthesis of 5-epi-trehazolin (trehalostatin).
  作者：YOSHIYUKI KOBAYASHI、HIDEKI MIYAZAKI、MASAO SHIOZAKI、HIDEYUKI HARUYAMA

  DOI：10.7164/antibiotics.47.932

  日期：——

  Synthesis of 5-epi-trehazolin (trehalostatin) (2) was accomplished via the crucial intermediate, epoxide (6α), from D-glucose. The stereochemistry of epoxide (6α) and its isomer (6β) which were obtained from Sharpless epoxidation, was determined by comparison between the NMR relaxation times of relevant protons.

  5-表-trehazolin（trehalostatin）（2）的合成是通过从D-葡萄糖中提取的关键中间体环氧化物（6α）完成的。通过比较相关质子的核磁共振弛豫时间，确定了从Sharpless环氧化反应中获得的环氧化物（6α）及其异构体（6β）的立体化学。
• Stereocontrolled Syntheses of 6-epi-Trehazolin and 6-epi-Trehalamine from D-Ribonolactone
  作者：Masao Shiozaki、Masami Arai、Yoshiyuki Kobayashi、Atsushi Kasuya、Shuichi Miyamoto、Youji Furukawa、Tomoko Takayama、Hideyuki Haruyama

  DOI：10.1021/jo00095a021

  日期：1994.8

  6-epi-Trehazolin was synthesized in a stereocontrolled manner, and this synthesis proved that an oxazine structural isomer of 6-epi-trehazolin does not exist.