2-(trimethylsilyl)ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside | 117253-40-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: 2-(Trimethylsilyl) ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside；2-(Trimethylsilyl)-ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside；(2R,3R,4R,5S,6R)-5-[[(3aS,4R,6S,7R,7aR)-7-hydroxy-4-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-6-(hydroxymethyl)-2-(2-trimethylsilylethoxy)oxane-3,4-diol
• CAS: 117253-40-4
• 化学式: C₂₀H₃₈O₁₁Si
• 分子量: 482.601
• InChiKey: QFNKSOCAEQGUFC-DTIYSIMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium hydride 、 溶剂黄146 作用下， 反应 4.84h， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 2-(trimethylsilyl)ethyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• Substituted lactose and lactosamine derivatives as cell adhesion
  申请人：Glycomed Incorporated

  公开号：US05326752A1

  公开（公告）日：1994-07-05

  The compounds are of the formula ##STR1## wherein each R.sup.1 is independently H or lower alkyl (1-4C); R.sup.2 is H, lower alkyl (1-4C), alkylaryl or one or more additional saccharide residues; R.sup.3 and R.sup.4 are independently H, alkyl (1-6C), aryl or R.sup.3 and R.sup.4, taken together, form a five or six-membered ring optionally containing a hetroatom selected from the group consisting of O, S, and NR.sup.1 ; wherein said five- or six-membered ring may further be substituted by one or more substituents selected from the group consisting of (CHOR.sup.1).sup.m H wherein m is 1-4, OR.sup.1, OOCR.sub.1, NR.sup.1, NCOR.sup.1 and SR.sup.1 ; Y is H, OR.sup.1, OOCR.sup.1, NR.sup.1.sub.2, NCOR.sub.1 or SR.sub.1 ; and X is --CHR.sup.5 (CHOR.sup.1).sub.2 CHR.sup.6 OR.sup.1 wherein R.sup.5 and R.sup.6 are independently H, lower alkyl (1-4C) optionally substituted with one or more R, or result in a five- or six-membered ring optionally containing a heteroatom selected from the group consisting of O, S and NR.sup.1 ; said five or six-membered ring optionally substituted with one substituent selected from the group consisting of R.sup.1, CHOR.sup.1, OR.sup.1, OOCR.sup.1, NR.sup.1.sub.2, NHCOR.sup.1, SR.sup.1 and F; or X is benzoyl or naphthoyl having 1-3 hydroxyl substituents, with the proviso that if X represents a hexose substituent R.sup.3 and R.sup.4, taken together, cannot provide a hexose substituent. These compounds are useful in the treatment of conditions characterized by excess inflammation.

  这些化合物的化学式为##STR1## 其中每个R.sup.1独立地为H或较低的烷基（1-4C）；R.sup.2为H，较低的烷基（1-4C），烷基芳基或一个或多个额外的糖残基；R.sup.3和R.sup.4独立地为H，烷基（1-6C），芳基或R.sup.3和R.sup.4在一起形成一个五元或六元环，可选地包含从O、S和NR.sup.1组成的杂原子；其中所述的五元或六元环可以进一步被来自羟甲氧基（CHOR.sup.1）.sup.m H的一个或多个取代基取代，其中m为1-4，OR.sup.1，OOCR.sub.1，NR.sup.1，NCOR.sup.1和SR.sup.1；Y为H，OR.sup.1，OOCR.sup.1，NR.sup.1.sub.2，NCOR.sub.1或SR.sub.1；X为--CHR.sup.5（CHOR.sup.1）.sub.2 CHR.sup.6 OR.sup.1，其中R.sup.5和R.sup.6独立地为H，较低的烷基（1-4C），可选地用一个或多个R取代，或形成一个五元或六元环，可选地包含从O、S和NR.sup.1组成的杂原子；所述的五元或六元环可用来自R.sup.1、CHOR.sup.1、OR.sup.1、OOCR.sup.1、NR.sup.1.sub.2、NHCOR.sup.1、SR.sup.1和F的一个取代基进行取代；或者X为有1-3个羟基取代的苯甲酰基或萘甲酰基，但前提是如果X代表一个己糖取代基，则R.sup.3和R.sup.4在一起不能提供一个己糖取代基。这些化合物在治疗过度炎症的情况下是有用的。
• A Practical Method for the Synthesis of Sialyl α-Glycosides
  作者：Valeri Martichonok、George M. Whitesides

  DOI：10.1021/ja960148b

  日期：1996.1.1

  Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0 degrees C affords the sialic acid donor alpha-2-(methylthio)-3-thiosialic acid 4 in quantitative yield. Sialylation of glycosyl accepters 9 and 10 with 4 in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40 degrees C gives alpha-sialosides in good yield and excellent stereoselectivity. No beta-sialosides are formed in either case. Removal of the auxiliary 3-(2,4-dimethylphenyl)-thio group is achieved in high yield using Ph(3)SnH and AIBN in refluxing toluene. Protected GM(3) trisaccharide and 6-sial-2-yllactose were obtained on a gram scale.
• A facile and regioselective synthesis of partially benzoylated 3',4'-O-isopropylidene-β-lactosides as standardized key intermediates for sialyl Lewis X (sLex) analogues
  作者：Mina A. Nashed、John H. Musser

  DOI：10.1016/0008-6215(93)84013-v

  日期：1993.12
• JANSSON, KARL;AHLFORS, STEFAN;FREJD, TORBJORN;KIHLBERG, JAN;MAGNUSSON, GO+, J. ORG. CHEM., 53,(1988) N 24, C. 5629-5647
  作者：JANSSON, KARL、AHLFORS, STEFAN、FREJD, TORBJORN、KIHLBERG, JAN、MAGNUSSON, GO+

  DOI：——

  日期：——
• 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars
  作者：Karl Jansson、Stefan Ahlfors、Torbjoern Frejd、Jan Kihlberg、Goeran Magnusson、Jan Dahmen、Ghazi Noori、Kristina Stenvall

  DOI：10.1021/jo00259a006

  日期：1988.11