ethyl 6-O-trityl-1-thio-β-D-galactopyranoside | 311797-15-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl 6-O-trityl-1-thio-β-D-galactopyranoside
• CAS: 311797-15-6
• 化学式: C₂₇H₃₀O₅S
• 分子量: 466.598
• InChiKey: ODHXWVMEHURSSF-CAKRBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 6-O-trityl-1-thio-β-D-galactopyranoside 在 硫酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 、 mineral oil 为溶剂， 反应 21.25h， 生成 ethyl 2-O-benzyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  海洋糖鞘脂Vesparioside B的全合成

  摘要：

  海洋糖脂 vesparioside B 的主要成分的首次全合成（方案 1, 1, R1 = n-C22H45, R2 = n-C14H29）已通过收敛 [4 + 3] 耦合策略完成。关键步骤包括立体选择性安装一组具有挑战性的 1,2-顺式糖苷键。分别开发了 2-喹啉羰基辅助的 α-半乳糖基化和新型 β-阿拉伯糖基化，以合成 α-呋喃半乳糖苷和 β-阿拉伯吡喃糖苷键。此外，4,6-O-亚苄基控制的α-吡喃半乳糖基化反应允许左侧四糖供体2与右侧二糖脂质受体3有效连接，从而导致1的全合成。

  DOI：

  10.1021/jacs.5b12589
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 ethyl 6-O-trityl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of Homogalacturonan Fragments

  摘要：

  Glycosylation of the D-galacturonic acid ester derivatives 15 and 17, which are prepared directly from D-galacturonic acid, with the thioglycosides 28 and 32, derived from the same sugar, provides alpha(1-->4)-linked dimers. The formation of the glycosidic linkage between the galacturonic acid moieties is best achieved by iodonium di-sym-collidine perchlorate promotion. Thus, the 4'-O-p-methoxybenzyl dimer 38 can be obtained in 64% yield. Partial deprotection of the 4'-O-position provided the glycosyl acceptor 36, which was coupled with the donor 32 to yield the alpha(1 "-->4')-linked trimer 39 (48%). Approximately 8% of the beta(1 "-->4')-coupled isomer was observed in the C-13 NMR spectrum of the reaction mixture.

  DOI：

  10.1080/07328300008544125

文献信息

• Synthesis of the <i>Leishmania</i> LPG Core Heptasaccharyl <i>myo</i>-Inositol
  作者：Katinka Ruda、Jan Lindberg、Per J. Garegg、Stefan Oscarson、Peter Konradsson

  DOI：10.1021/ja001515t

  日期：2000.11.1

  Total synthesis of the core heptasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)[Glcp(alpha1-PO4-6)Manp](alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, and the corresponding hexasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)Manp(alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, found in the lipophosphoglycans of Leishmania parasites are described. The target molecules contain synthetic challenges such as an unusual internal galactofuranosyl residue and an anomeric phosphodiester. The synthesis was accomplished using a convergent block synthetic strategy. Four building blocks, a trigalactoside, a dimannoside, a glucosyl inositolphosphate, and a glucosyl-alpha -1-H-phosphonate, all appropriately protected, were used. The trigalactoside was linked to the dimannoside followed by glycosylation with the glucosyl inositolphosphate to produce the fully protected hexasaccharyl myo-inositol. Subsequent oxidative coupling of the glucosyl-H-phosphonate formed the anomeric phosphodiester linkage to produce the protected heptasaccharyl myo-inositol. Both the assembly order of the subunits and sequence of deprotection were essential for the successful synthesis of these complex molecules. The deprotection was accomplished by deacetylation and clevage of benzyl ethers with sodium in liquid ammonia, followed by acidic deacetalization/desilylation to produce the target molecules.
• Semi-orthogonality of O-pentenyl and S-ethyl glycosides: application for the oligosaccharide synthesis
  作者：Alexei V. Demchenko、Cristina De Meo

  DOI：10.1016/s0040-4039(02)02235-9

  日期：2002.12

  Novel semi-orthogonal glycosylation strategy with the use of 0-pentenyl and thioglycosides has been developed. According to this technique both armed and disarmed thioglycosides can be selectively activated with MeOTf in the presence of either armed or disarmed 0-pentenyl glycosides. The applicability of this novel strategy for the synthesis of a trans-cis glycosylation pattern, not accessible via conventional armed-disarmed approach, has been demonstrated for the synthesis of a linear tetrasaccharide derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.