methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside | 64495-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: methyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-methylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 64495-86-9
• 化学式: C₂₇H₃₈O₁₇S
• 分子量: 666.655
• InChiKey: QEZSKZFOLCYLGI-JIAHTRGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.03
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  211.79
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 甲醇 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.0h， 生成 methyl 4-O-(4,6-O-isopropylidene-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective Synthesis oftrans-1,2-Di-O-acetyl Glycoses

  摘要：

  通过用乙酸三甲基甲硅烷基酯处理，可以以高度立体选择性的方式将吡喃己糖的1,2-O-(1-甲氧基亚乙基)衍生物转化为相应的反式-1,2-二乙酸酯。 O-乙酰基、O-苄基和O-异亚丙基在反应条件下是稳定的。

  DOI：

  10.1055/s-1990-26995
• 作为产物：
  描述：

  lactose octaacetate 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Streamlined Synthesis of Per-O-acetylated Sugars, Glycosyl Iodides, or Thioglycosides from Unprotected Reducing Sugars¹

  摘要：

  Solvent-free per-O-acetylation of sugars with stoichiometric acetic anhydride and catalytic iodine proceeds in high yield (90-99%) to give exclusively pyranose products as anomeric mixtures. Without workup, subsequent anomeric substitution employing iodine in the presence of hexamethyldisilane (i.e., TMS-I generated in situ) gives the corresponding glycosyl iodides in 75-95% isolated yield. Alternatively, and without workup, further treatment with dimethyl disulfide or thiol (ethanethiol or thiocresol) gives anomerically pure thioglycosides in more than 75% overall yield.

  DOI：

  10.1021/jo048890e

文献信息

• A Through-process for the Preparation of Methyl Per-<i>O</i>-acetyl 1-Thio-glycosides from Aldoses
  作者：Shinkiti Koto、Toyosaku Yoshida、Kazuhiro Takenaka、Shonosuke Zen

  DOI：10.1246/bcsj.55.3667

  日期：1982.11

  d-Glucose, d-galactose, d-mannose, d-xylose, l-arabinose, l-fucose, l-rhamnose, maltose, cellobiose, lactose, d-glucosamine, d-galactosamine, and d-mannosamine were converted into the corresponding methyl per-O-acetyl 1-thioglycopyranosides by way of a three-step (acetobromination, methylthioation, and acetylation) through-process in a single vessel.

  d-葡萄糖、d-半乳糖、d-甘露糖、d-木糖、l-阿拉伯糖、l-岩藻糖、l-鼠李糖、麦芽糖、纤维二糖、乳糖、d-葡萄糖胺、d-半乳糖胺和d-甘露糖胺通过一个反应器经过三步（溴乙酰化、甲硫化和乙酰化）转化为相应的甲基全乙酰化1-硫代糖呋喃糖苷。
• Synthesis of the methyl and 1-octyl glycosides of the P-antigen tetrasaccharide (globotetraose)
  作者：Karin Leontein、Marianne Nilsson、Thomas Norberg

  DOI：10.1016/s0008-6215(00)90671-2

  日期：1985.12

  The methyl and 1-octyl beta-glycosides of the P-antigen tetrasaccharide [globotetraose, beta-D-GalpNAc-(1----3)-alpha-D-Galp-(1----4)-beta-D-Galp-(1----4) -D-Glc] were synthesised from a tetrasaccharide precursor, prepared using methyl disaccharide 1-thioglycosides as intermediates. In the key glycosidation with silver triflate, HO-2 was used as an alpha-directing group in the glycosyl bromide.

  P-抗原四糖[globotetraose，beta-D-GalpNAc-（1 ---- 3）-alpha-D-Galp-（1 ---- 4）-beta-的甲基和1-辛基β-糖苷由四糖前体合成了D-Galp-（1 ---- 4）-D-Glc]，该前体是使用甲基二糖1-硫代糖苷为中间体制备的。在三氟甲磺酸银的关键糖苷化中，HO-2被用作糖基溴化物中的α-导向基团。
• An efficient approach to O-glycosides through CuBr2-Bu4NBr mediated activation of glycosides
  作者：Susumu Sato、Masato Mori、Yukishige Ito、tomoya Ogawa

  DOI：10.1016/s0008-6215(00)90163-0

  日期：1986.11
• POZSGAY, VINCE;JENNINGS, HAROLD J., SYNTHESIS,(1990) N, C. 724-726
  作者：POZSGAY, VINCE、JENNINGS, HAROLD J.

  DOI：——

  日期：——