D-葡萄糖-二乙基缩硫醛 | 1941-52-2

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: D-葡萄糖-二乙基缩硫醛
• 中文别名: D-葡萄糖二乙基缩硫醛
• 英文名称: D-glucose diethyl mercaptal
• 英文别名: D-glucose diethyl dithioacetal；diethyl dithioacetal D-glucose；(2R,3R,4S,5R)-6,6-bis(ethylsulfanyl)hexane-1,2,3,4,5-pentol
• CAS: 1941-52-2
• 化学式: C₁₀H₂₂O₅S₂
• 分子量: 286.414
• InChiKey: BTOYCPDACQXQRS-LURQLKTLSA-N

物化性质

• 熔点：
  126-130 °C
• 沸点：
  398.77°C (rough estimate)
• 密度：
  1.3416 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  152
• 氢给体数：
  5
• 氢受体数：
  7

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S24/25
• 危险类别码：
  R20/21/22,R36/38,R63,R21,R62,R46
• WGK Germany：
  3
• 海关编码：
  29400000

反应信息

• 作为反应物：
  描述：

  D-葡萄糖-二乙基缩硫醛 在 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 1-去氧-D-山梨醇
  参考文献：
  名称：

  Identification of catabolic pathway for 1-deoxy-D-sorbitol in Bacillus licheniformis

  摘要：

  1-Deoxy-D-sorbitol, the 1-deoxy analogue of D-sorbitol, has been detected in human urine as well as in natural herbs and spices. Although there are sporadic reports about 1-deoxy-D-sorbitol dehydrogenase, the complete catabolic pathway of 1-deoxy-D-sorbitol remains unsolved. Informed by the promiscuous activities of fructose-6-phosphate aldolase (FSA) which is involved in the sorbitol (glucitol) utilization (gut) operon and guided by the large scale bioinformatics analysis, we predicted and then experimentally verified the gut operon encoded by Bacillus licheniformis ATCC14580 is responsible for the catabolism of both D-sorbitol and 1-deoxy-D-sorbitol by in vitro activity assays of pathway enzymes, in vivo growth phenotypes, and transcriptomic studies. Moreover, the phylogenetic distribution analysis suggests that the D-sorbitol and 1-deoxy-D-sorbitol catabolic gene cluster is mostly conserved in members of Firmicutes phylum.

  DOI：

  10.1016/j.bbrc.2021.11.072
• 作为产物：
  描述：

  葡萄糖 生成 D-葡萄糖-二乙基缩硫醛
  参考文献：
  名称：

  PAZUR J. H.; MISKIEL F. J.; LIU B., J. CHROMATOGR., 396,(1987) 139-147

  摘要：

  DOI：

文献信息

• Bromodimethylsulfonium bromide (BDMS) mediated dithioacetalization of carbohydrates under solvent-free conditions
  作者：Abu T. Khan、Md. Musawwer Khan

  DOI：10.1016/j.carres.2010.07.044

  日期：2010.10

  A variety of diethyl dithioacetals of sugars can be prepared in very good yields by the reaction of various monosaccharides with ethanethiol in the presence of 3 mol% bromodimethylsulfonium bromide (BDMS) at 0-5 degrees C. Similarly, dipropyl dithioacetal derivatives can also be obtained in good yields using propanethiol under identical reaction conditions. These dithioacetal derivatives were characterized

  通过使各种单糖与乙硫醇在3 mol％溴化二甲基ulf溴化物（BDMS）的存在下，在0-5℃下反应，可以以很高的收率制得各种糖类的二乙基二硫缩醛。类似地，也可以得到二丙基二硫缩醛衍生物在相同的反应条件下，使用丙硫醇可得到良好的收率。这些二硫缩醛衍生物的特征在于，使用硅胶负载的高氯酸进行过O-乙酰化。本方案的显着特征是良好至优异的收率，温和，清洁和无溶剂的反应条件。该方法非常适合大规模制备各种糖的二硫缩醛衍生物。
• THE OXIDATION OF SUGAR ACETALS AND THIOACETALS BY ACETOBACTER SUBOXYDANS
  作者：D. T. Williams、J. K. N. Jones、N. J. Dennis、R. J. Ferrier、W. G. Overend

  DOI：10.1139/v65-123

  日期：1965.4.1

  The oxidation by Acetobacter suboxydans of several aldose dimethylacetals and diethyldithioacetals has been achieved. Isolation and characterization of the ketose products showed that the oxidation...

  已经实现了几种醛糖二甲基缩醛和二乙基二硫代缩醛的氧化醋杆菌氧化。酮糖产物的分离和表征表明氧化...
• Regioselective Synthesis of Difluorinated <i>C</i>-Furanosides Involving a Debenzylative Cycloetherification
  作者：Julien A. Delbrouck、Valentin N. Bochatay、Abdellatif Tikad、Stéphane P. Vincent

  DOI：10.1021/acs.orglett.9b01878

  日期：2019.7.19

  A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences

  本文描述了由未保护的醛糖通过由三氟乙二氨基氨基硫醚诱导的脱苄基环醚化（DBCE）反应高度区域选择性地合成有价值的宝石-二氟化C-呋喃糖苷的方法。使用一系列可商购的戊糖和己糖描述了该DBCE反应的范围和局限性，以在没有选择性保护/脱保护序列的情况下以中等至良好的产率提供了相应的宝石-二氟化C-呋喃糖苷。
• Prodrugs of L-cysteine as protective agents against acetaminophen-induced hepatotoxicity. 2-(Polyhydroxyalkyl)- and 2-(polyacetoxyalkyl)thiazolidine-4(R)-carboxylic acids
  作者：Jeanette C. Roberts、Herbert T. Nagasawa、Richard T. Zera、Robert F. Fricke、David J. W. Goon

  DOI：10.1021/jm00393a034

  日期：1987.10

  prodrugs of L-cysteine (1a-h) were synthesized by the condensation of the sulfhydryl amino acid with naturally occurring aldose monosaccharides containing three, five, and six carbon atoms. The resulting 2-(polyhydroxyalkyl)thiazolidine-4(R)-carboxylic acids (TCAs) are capable of releasing L-cysteine and the sugars by nonenzymatic ring opening and hydrolysis. Thus, when added to rat hepatocyte preparations

  通过巯基氨基酸与天然存在的含三个，五个和六个碳原子的醛糖单糖的缩合，合成了八个L-半胱氨酸的前药（1a-h）。所得的2-（聚羟基烷基）噻唑烷-4（R）-羧酸（TCA）能够通过非酶开环和水解而释放L-半胱氨酸和糖。因此，当将它们添加到体外大鼠肝细胞制剂中时，这些TCA（1.0 mM）相对于对照组将细胞谷胱甘肽（GSH）的水平提高了1.2-2.1倍。基于这一发现，在小鼠模型中测试了半胱氨酸前药作为对乙酰氨基酚诱导的肝毒性的保护剂。衍生自D-核糖和L-半胱氨酸的TCA（RibCys，1d）显示了该系列的最大治疗前景，存活率为100％（12/12），而未经治疗的为17％。但是，这些前药对大鼠肝细胞中GSH产生的刺激程度与对小鼠的保护程度无关，这表明药代动力学参数必须在体内超越。为了评估脂质溶解度增加的效果，我们通过在缩合反应中使用过乙酰化醛糖制备了前药2a-c。然而，这些化合物对小鼠表现出急性毒性
• [EN] A NOVEL PROCESS FOR THE PREPARATION OF SGLT-2 INHIBITORS<br/>[FR] NOUVEAU PROCÉDÉ DE PRÉPARATION D'INHIBITEURS DE SGLT-2
  申请人：PHARMATHEN SA

  公开号：WO2020001812A1

  公开（公告）日：2020-01-02

  The present invention relates to a novel process for the preparation of SGLT-2 inhibitors via addition of a hydroxymethylene group in an open chain intermediate, readily accessible from D-glucose.

  本发明涉及一种通过在开链中间体中引入羟甲基烯基来制备SGLT-2抑制剂的新方法，该开链中间体可容易地从D-葡萄糖获得。

表征谱图