(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol | 200191-55-5

• 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: (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol
• 英文别名: (3S,4R,5S,6S)-6-(hydroxymethyl)-4,5-bis(phenylmethoxy)thian-3-ol
• CAS: 200191-55-5
• 化学式: C₂₀H₂₄O₄S
• 分子量: 360.474
• InChiKey: XICBCZSQZITQQR-IYWMVGAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以84%的产率得到2,6-anhydro-2-thio-D-glucitol
  参考文献：
  名称：

  硫糖作为糖苷酶的弱抑制剂的合成

  摘要：

  一系列对映体纯的硫糖（1,6-dideoxy-1,6-thio-D-甘露醇或L-iditol，1,5-dideoxy-1,5-thio-L-gulitol或D-葡萄糖醇和2,5 -二脱氧-2，5-硫代-L-ID醇或D-甘露醇，及其相应的亚砜或砜）是通过C 2对称双环氧化物的硫环化合成的，随后在少数情况下随后进行环异构化。这些化合物已被评估为几种糖苷酶（α-和β-D-葡萄糖苷酶，α-D-甘露糖苷酶和α-L-岩藻糖苷酶）的抑制剂。

  DOI：

  10.1016/s0040-4020(97)10096-5
• 作为产物：
  描述：

  Benzoic acid (2S,3S,4R,5S)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-thiopyran-2-ylmethyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(3S,4R,5S,6S)-4,5-Bis-benzyloxy-6-hydroxymethyl-tetrahydro-thiopyran-3-ol
  参考文献：
  名称：

  硫糖作为糖苷酶的弱抑制剂的合成

  摘要：

  一系列对映体纯的硫糖（1,6-dideoxy-1,6-thio-D-甘露醇或L-iditol，1,5-dideoxy-1,5-thio-L-gulitol或D-葡萄糖醇和2,5 -二脱氧-2，5-硫代-L-ID醇或D-甘露醇，及其相应的亚砜或砜）是通过C 2对称双环氧化物的硫环化合成的，随后在少数情况下随后进行环异构化。这些化合物已被评估为几种糖苷酶（α-和β-D-葡萄糖苷酶，α-D-甘露糖苷酶和α-L-岩藻糖苷酶）的抑制剂。

  DOI：

  10.1016/s0040-4020(97)10096-5

文献信息

• Thiosugars from D-mannitol
  作者：Myrielle Fuzier、Yves Le Merrer、Jean-Claude Depezay

  DOI：10.1016/0040-4039(95)01273-k

  日期：1995.9

  Enantiomerically pure thiosugars, with a thiepan, tetrahydrothiopyrum or tetrahydrothiophene backbone, have been synthesized by thio-heterocyclization of enantiopure C-2-symmetric bis-epoxides and possibly ring contraction.
• Heterocyclisation of free or partially protected alditols via their bis-cyclic sulfate derivatives. Versatile synthesis of aza and thiodeoxyanhydroalditol with erythro, threo, arabino, gulo, talo or manno configuration
  作者：Virginie Glaçon、Mohammed Benazza、Daniel Beaupère、Gilles Demailly

  DOI：10.1016/s0040-4039(00)00791-7

  日期：2000.6

  The bis-cyclic sulfate derivatives of erythritol (1), D,L-threitol (5), 3,4-di-O-benzyl-D-mannitol (9), 1,2-O-isopropylidene-D-mannitol (14) and 1-O-benzyl-D,L-xylitol (18) were submitted to nucleophilic attack by allylamine or sodium sulfide. In both cases, heterocyclisation occurred and aza or thioanhydrodeoxyalditols were obtained in moderate to good yields (40 to 89%). With compound 9, 1,5-anhydro-5-thio-L-gulitol (12) was obtained as the main product, a result that is in contrast with previous results reported in the literature using bis-epoxide as bielectrophile intermediate.(1) (C) 2000 Published by Elsevier Science Ltd.
• Synthesis of thiosugars as weak inhibitors of glycosidases
  作者：Yves Le Merrer、Myrielle Fuzier、Isabelle Dosbaa、Marie-José Foglietti、Jean-Claude Depezay

  DOI：10.1016/s0040-4020(97)10096-5

  日期：1997.12

  enantiomerically pure thiosugars (1,6-dideoxy-1,6-thio-D-mannitol or L-iditol, 1,5-dideoxy-1,5-thio-L-gulitol or D-glucitol and 2,5-dideoxy-2,5-thio-L-iditol or D-mannitol, and their corresponding sulfoxide or sulfone) was synthesized via thiocyclization of C2-symmetric bis-epoxides, and subsequently followed by ring isomerization in few cases. These compounds have been evaluated as inhibitors of several

  一系列对映体纯的硫糖（1,6-dideoxy-1,6-thio-D-甘露醇或L-iditol，1,5-dideoxy-1,5-thio-L-gulitol或D-葡萄糖醇和2,5 -二脱氧-2，5-硫代-L-ID醇或D-甘露醇，及其相应的亚砜或砜）是通过C 2对称双环氧化物的硫环化合成的，随后在少数情况下随后进行环异构化。这些化合物已被评估为几种糖苷酶（α-和β-D-葡萄糖苷酶，α-D-甘露糖苷酶和α-L-岩藻糖苷酶）的抑制剂。