methyl 3,4-O-isopropylidene-6-O-tosyl-α-D-galactopyranoside | 34698-20-9

• 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: methyl 3,4-O-isopropylidene-6-O-tosyl-α-D-galactopyranoside
• 英文别名: methyl 3,4-O-isopropylidene-6-O-(p-toluenesulfonyl)-α-D-galactopyranoside；methyl-[O³,O⁴-isopropylidene-O⁶-(toluene-4-sulfonyl)-α-D-galactopyranoside；Methyl-[O³,O⁴-isopropyliden-O⁶-(toluol-4-sulfonyl)-α-D-galactopyranosid；[(3aS,4R,6S,7R,7aR)-7-hydroxy-6-methoxy-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methyl 4-methylbenzenesulfonate
• CAS: 34698-20-9
• 化学式: C₁₇H₂₄O₈S
• 分子量: 388.439
• InChiKey: XCYNJCRDVMCBCG-LJIZCISZSA-N

物化性质

• 沸点：
  549.0±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.95
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  100.52
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-tosyl-α-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以77%的产率得到methyl 6-azido-6-deoxy-3,4-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of glycose carbamides and evaluation of the induction of erythroid differentiation of human erythroleukemic K562 cells

  摘要：

  A series of carbamides derived from 1,2:5,6-di-O-isopropylidene-D-gluco- (1) and D-allofuranose (3) as well as their 5,6-O-deprotected analogues (2 and 4) and methyl 3,4-O-isopropylidene-alpha- and beta-D-galactopyranosides (5 and 6) have been prepared in order to evaluate their ability to induce erythroid differentiation of human erythroleukemic K562 cells. Twenty out of 51 carbamides tested exhibit an appreciable activity as inducers of erythroid differentiation and have been fully characterized and described. (c) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.05.001
• 作为产物：
  描述：

  methyl 6-O-tosyl-α-D-galactopyranoside 在 硫酸 、 丙酮 作用下， 生成 methyl 3,4-O-isopropylidene-6-O-tosyl-α-D-galactopyranoside
  参考文献：
  名称：

  58. 3：6-脱水半乳糖。第二部分 2-甲基和4-甲基3：6-脱水-α-甲基吡喃半乳糖苷

  摘要：

  DOI：

  10.1039/jr9440000229

文献信息

• Further Development of the Tin-Catalyzed Transcarbamoylation Reaction
  作者：Yoshiyasu Ichikawa、Tomoyuki Hasegawa、Takahiro Minami、Hiroshi Sato、Yukinori Morishita、Rika Ochi、Toshiya Masuda

  DOI：10.1055/s-0040-1708020

  日期：2020.8

  Studies carried out to further develop tin-catalyzed trans­carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-­catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate

  为进一步开发锡催化的氨基甲酸酯化反应而进行的研究表明，在烯丙基氰酸酯到异氰酸酯重排的背景下，肉桂醇的氨基甲酸酯化可以有效地在10克规模上进行，并且锡催化的氨基甲酸酯化是一种有价值的替代方法该方法使用三氯乙酰基异氰酸酯。此外，在锡催化的转氨甲酰化反应中发现氨基甲酸甲酯是一种经济的氨基甲酰基供体，该氨基甲酸酯显示出广泛的官能团耐受性，并简化了后处理程序。最后，开发了一种独特的合成方法来制备氨基甲酸酯系萜烯糖结合物。
• An Efficient Synthesis of Carbamates by Tin-Catalyzed Transcarbamoylation Reactions of Primary and Secondary Alcohols
  作者：Yoshiyasu Ichikawa、Yukinori Morishita、Shuhei Kusaba、Naoto Sakiyama、Yasunori Matsuda、Keiji Nakano、Hiyoshizo Kotsuki

  DOI：10.1055/s-0030-1258102

  日期：2010.7

  A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 °C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance.

  已经开发了一种基于锡催化氨基甲酰化过程合成氨基甲酸酯的新方法。伯醇和仲醇与氨基甲酸苯酯在 90 °C 的甲苯中在锡催化剂存在下顺利进行反应，以良好的产率生成相应的氨基甲酸酯。这种温和的方法表现出广泛的官能团耐受性。
• Dasgupta, F.; Singh, P. P.; Srivastava, H. C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 12, p. 1056 - 1059
  作者：Dasgupta, F.、Singh, P. P.、Srivastava, H. C.

  DOI：——

  日期：——
• Synthesis of Amino Sugars by Reduction of Hydrazine Derivatives; D- and L-Ribosamine, D-Lyxosamine^1-3
  作者：M. L. Wolfrom、F. Shafizadeh、R. K. Armstrong、T. M. Shen Han

  DOI：10.1021/ja01523a056

  日期：1959.7
• 2-METHYL-l-RHAMNOSE AND 2-METHYL-d-FUCOSE AND THEIR BEARING ON THE CONFIGURATION OF DIGITALOSE
  作者：HAROLD B. MacPHILLAMY、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01214a009

  日期：1939.5