ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside | 146530-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: Ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-beta-D-glucopyranoside；[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-6-ethylsulfanyl-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 146530-62-3
• 化学式: C₂₁H₂₈O₈S
• 分子量: 440.515
• InChiKey: IJZVXCYUBMKLKT-ADAARDCZSA-N

物化性质

• 熔点：
  112-114 °C(Solv: toluene (108-88-3); heptane (142-82-5))
• 沸点：
  531.1±50.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside 在 三氟甲磺酸 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 145.0h， 生成 ethyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Ethyl 2-Azido-2-deoxy-1-thio-β-d-mannopyranosides 的制备及其重排为 2-S-Ethyl-2-thio-β-d-mannopyranosylamines

  摘要：

  乙基 2-azido-2-deoxy-1-thio-β-D-mannopyranosides 7-11 的合成，从具有葡萄糖构型的适当合成子开始，通过 C(2) 处的 SN 2 取代，并将它们重排为 2-S介绍了-乙基-2-硫代-β-D-吡喃甘露糖胺 12-14。

  DOI：

  10.1055/s-2006-926297
• 作为产物：
  描述：

  1,2,4,6-四-o-乙酰基-3-o-苄基-beta-d-吡喃葡萄糖 、 乙硫醇 在 molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到ethyl 2,4,6-tri-O-acetyl-3-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  与肝素和硫酸乙酰肝素有关的三糖和四糖的甲基糖苷的合成

  摘要：

  从肝素中分离出的四糖的甲基糖苷，甲基O-（α-L-氨基吡喃糖基糖醛酸）-（1-> 4）-O-（2-乙酰氨基-2-脱氧-α-D-葡萄糖基吡喃糖基）-（1 -> 4）-O-（β-D-吡喃葡萄糖基尿酸）-（1> 3）-O-β-D-吡喃半乳糖苷二钠盐及其三糖衍生物，甲基O-（α-L-吡喃基葡萄糖醛酸）-（1-> 4）-O-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-（1-> 4）-O-β-D-吡喃葡萄糖基糖醛酸二钠盐合成块型策略。合适的被保护的艾杜糖醛酸和葡糖胺的二糖嵌段（IdoA-GlcN）用作合成的关键中间体，并与被保护的半乳糖衍生物和葡糖醛酸和半乳糖的二糖嵌段（GlcA-Gal）糖基化，得到三-和四糖衍生物。

  DOI：

  10.1016/0008-6215(93)84030-a

文献信息

• Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors
  作者：Qingchao Liu、Tiantian Guo、Fahui Li、Dong Li

  DOI：10.1039/c6nj01602b

  日期：——

  The first synthesis of the triterpenoid saponin 1 and its derivatives 2–3 was efficiently achieved in an efficient and practical strategy with an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and a N-phenyltrifluoroacetimidate donor as a key step, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. The preliminary structure–activity relationship

  以无味的2-甲基-5-叔丁基苯基（Mbp）硫代糖苷和N-苯基三氟乙酰亚氨酸酯供体为关键步骤，有效而有效地实现了三萜皂苷1及其衍生物2-3的首次合成，和它们对α葡糖苷酶和α淀粉酶抑制活性进行评价体外。初步的结构-活性关系研究表明，C4-CHO和C4-CH 2 OH对α-葡萄糖苷酶抑制活性不是必需的。在这三种化合物中，化合物3表现出对α-葡萄糖苷酶的显着抑制活性，IC 50为值为9.17μM。根据Dixon图上的截距确定为9.35μM的K i，抗α-葡萄糖苷酶的更强皂苷3可能是非竞争性抑制模式。同时，计算化合物1-3的亲脂性，作为药理效力的预测。根据预测的log  P值，亲脂性可能与评估的生物学潜能相关。
• Multi-Gram Synthesis of a Hyaluronic Acid Subunit and Synthesis of Fully Protected Oligomers
  作者：Mickaël Virlouvet、Michael Gartner、Katarzyna Koroniak、Jonathan P. Sleeman、Stefan Bräse

  DOI：10.1002/adsc.201000008

  日期：2010.10.4

  Fully protected tetra-, hexa- and octasaccharides of hyaluronic acid were synthesized on a scale of several 100 mg up to gram quantities using allyl (methyl 2-O-benzoyl-3-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronate)-(13)-4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside as a key building block. This disaccharide was subjected to deprotection, then glycosylation via the trichloroacetimidate

  使用烯丙基（甲基2 - O-苯甲酰基-3 - O-苄基-4 - O-乙酰丙酰基-β - D）以几百毫克至几克的量合成透明质酸的完全保护的四糖，六糖和八糖-glucopyranosyluronate） - （13）-4- ø -乙酰基-6- ø -苄基-2-脱氧-2- trichloroacetamido- β -D-吡喃葡萄糖苷作为关键构建块。对该二糖进行脱保护，然后通过三氯乙酰亚胺酸酯方法进行糖基化以形成寡糖。
• Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens
  作者：Thomas Ziegler、Elisabeth Eckhardt、Veronique Birault

  DOI：10.1021/jo00057a021

  日期：1993.2

  A series of 2,3-di-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-D-glucopyranosyl donors (beta-phenylthio 3, bromide 4, alpha-chloride 5, beta-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding alpha-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-beta-D-glucopyranoside 10 to give the disaccharide 11. Best results with respect to yield and beta-selectivity of the coupling were achieved with imidate 7. Thus, the 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide. Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-[(benzyloxycarbonyl)amino]pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18. Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26. The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-alpha-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40. Next, NIS-mediated condensation of 40 and 5-[(benzyloxycarbonyl)amino]pentanol followed by deblocking gave 42. Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.
• Preparation of Ethyl 2-Azido-2-deoxy-1-thio-β-<scp>d</scp>-mannopyranosides, and their Rearrangement to 2-<i>S</i>-Ethyl-2-thio-β-<scp>d</scp>-mannopyranosylamines
  作者：Miroslav Ledvina、Jan Veselý、Anna Rohlenová、Martina Džoganová、Tomáš Trnka、Iva Tišlerová、David Šaman

  DOI：10.1055/s-2006-926297

  日期：——

  The synthesis of ethyl 2-azido-2-deoxy-1-thio-β-D-mannopyranosides 7-11, starting from appropriate synthons with gluco configuration, via S N 2 substitution at C(2), and their rearrangement to 2-S-ethyl-2-thio-β-D-mannopyranosylamines 12-14 are presented.

  乙基 2-azido-2-deoxy-1-thio-β-D-mannopyranosides 7-11 的合成，从具有葡萄糖构型的适当合成子开始，通过 C(2) 处的 SN 2 取代，并将它们重排为 2-S介绍了-乙基-2-硫代-β-D-吡喃甘露糖胺 12-14。
• Synthesis of the methyl glycosides of a tri- and a tetra-saccharide related to heparin and heparan sulphate
  作者：Marianne Nilsson、Carl-Magnus Svahn、Jacob Westman

  DOI：10.1016/0008-6215(93)84030-a

  日期：1993.8

  The methyl glycoside of a tetrasaccharide isolated from heparin, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2-deoxy-alpha-D- glucopyranosyl)-(1-->4)-O-(beta-D-glucopyranosyluronic acid)-(1-->3)-O-beta-D-galactopyranoside disodium salt and a trisaccharide derivative thereof, methyl O-(alpha-L-idopyranosyluronic acid)-(1-->4)-O-(2-acetamido-2- deoxy-alpha-D-glucopyranosyl)-(1-

  从肝素中分离出的四糖的甲基糖苷，甲基O-（α-L-氨基吡喃糖基糖醛酸）-（1-> 4）-O-（2-乙酰氨基-2-脱氧-α-D-葡萄糖基吡喃糖基）-（1 -> 4）-O-（β-D-吡喃葡萄糖基尿酸）-（1> 3）-O-β-D-吡喃半乳糖苷二钠盐及其三糖衍生物，甲基O-（α-L-吡喃基葡萄糖醛酸）-（1-> 4）-O-（2-乙酰氨基-2-脱氧-α-D-吡喃葡萄糖基）-（1-> 4）-O-β-D-吡喃葡萄糖基糖醛酸二钠盐合成块型策略。合适的被保护的艾杜糖醛酸和葡糖胺的二糖嵌段（IdoA-GlcN）用作合成的关键中间体，并与被保护的半乳糖衍生物和葡糖醛酸和半乳糖的二糖嵌段（GlcA-Gal）糖基化，得到三-和四糖衍生物。