(1Ξ)-D-O²,O³,O⁴,O⁵,O⁶-pentaacetyl-S-ethyl-1-chloro-1-thio-galactitol | 5160-11-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1Ξ)-D-O²,O³,O⁴,O⁵,O⁶-pentaacetyl-S-ethyl-1-chloro-1-thio-galactitol
• 英文别名: (1Ξ)-D-O²,O³,O⁴,O⁵,O⁶-Pentaacetyl-S-aethyl-1-chlor-1-thio-galactit；[(2R,3S,4S,5R)-2,3,4,5-tetraacetyloxy-6-chloro-6-ethylsulfanylhexyl] acetate
• CAS: 5160-11-2
• 化学式: C₁₈H₂₇ClO₁₀S
• 分子量: 470.925
• InChiKey: RINRQEDWCUHMAH-CHVQCXDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  157
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (1Ξ)-D-O²,O³,O⁴,O⁵,O⁶-pentaacetyl-S-ethyl-1-chloro-1-thio-galactitol 在 molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 silver carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (2R,3S,4S,5R,6S)-6-Ethylsulfanyl-6-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-hexane-1,2,3,4,5-pentaol
  参考文献：
  名称：

  Use of Acyclic Glycosyl Donors for Furanoside Synthesis

  摘要：

  Treatment of the peracetylated ethyl dithioacetals of D-glucose, D-galactose, and D-mannose with acetyl chloride and boron trifluoride diethyl etherate at reflux yields the known acyclic 1-chlorol-(ethylthio) derivatives. These compounds are shown to effectively glycosylate a variety of carbohydrate accepters using silver trifluoromethanesulfonate as the promotor, affording stereospecifically the corresponding acyclic O,S-acetals in good to excellent yield. Furthermore, following deacetylation, treatment of these O,S-acetals with a mixture of mercuric salts in either methanol or dimethylformamide gives rise to disaccharides terminating in D-furanosyl residues.

  DOI：

  10.1021/jo9618583
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 、 乙醚 作用下， 生成 (1Ξ)-D-O²,O³,O⁴,O⁵,O⁶-pentaacetyl-S-ethyl-1-chloro-1-thio-galactitol
  参考文献：
  名称：

  d-Glucose S-Ethyl O-Methyl Monothioacetal

  摘要：

  DOI：

  10.1021/ja01868a099

文献信息

• The Synthesis of Disaccharides Terminating in D-Septanosyl Residues Using Acyclic Intermediates
  作者：Joseph C. McAuliffe、Ole Hindsgaul

  DOI：10.1055/s-1998-3128

  日期：1998.3

  A general method for the construction of disaccharides containing D-septanosyl residues from acyclic intermediates has been developed. The synthesis of an analogue of N-acetyl d-lactosamine with a d-galactoseptanosyl unit has also been accomplished with the aim of determining the behaviour of this compound as a substrate for several glycosyltransferases.

  已开发出一种通用方法，用于从开链中间体构建包含D-septanosyl残基的二糖。此外，还完成了一种N-乙酰D-乳糖胺类似物的合成，该类似物含有一个D-半乳糖septanosyl单元，旨在研究该化合物作为几种糖基转移酶底物的行为。
• Farkas,I. et al., Chemische Berichte, 1965, vol. 98, p. 1419 - 1426
  作者：Farkas,I. et al.

  DOI：——

  日期：——
• Monothioacetals of Galactose
  作者：M. L. Wolfrom、D. I. Weisblat

  DOI：10.1021/ja01861a046

  日期：1940.4