methyl 2,3,4-tri-O-benzoyl-6-O-(2-S-acetyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside | 627509-61-9

• 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-tri-O-benzoyl-6-O-(2-S-acetyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-4,5-dibenzoyloxy-2-[[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-acetylsulfanyloxan-2-yl]oxymethyl]-6-methoxyoxan-3-yl] benzoate
• CAS: 627509-61-9
• 化学式: C₄₂H₄₄O₁₇S
• 分子量: 852.867
• InChiKey: VJMHCOLHOLWGPL-RHZQRUEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-(2-S-acetyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside 在 sodium methylate 、 镍 作用下， 以 甲醇 、 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Glycosylation with 2′-thio-S-acetyl participation

  摘要：

  The reaction of 1,2,3,4,6-penta-O,S,O,O,O-acetyl-2-thio-beta-D-glucopyranose with glycosyl acceptors in the presence of trimethylsilyl triflate leads to the beta-disaccharides exclusively, owing to especially avid anchimeric assistance by the 2-thio-S-acetyl group. Optional reductive removal of -SAc with Ra-Ni gives the corresponding 2'-deoxy-beta-disaccharides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.063
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-2,5-diacetoxy-6-acetoxymethyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-4-yl ester 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 methyl 2,3,4-tri-O-benzoyl-6-O-(2-S-acetyl-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Glycosylation with 2′-thio-S-acetyl participation

  摘要：

  The reaction of 1,2,3,4,6-penta-O,S,O,O,O-acetyl-2-thio-beta-D-glucopyranose with glycosyl acceptors in the presence of trimethylsilyl triflate leads to the beta-disaccharides exclusively, owing to especially avid anchimeric assistance by the 2-thio-S-acetyl group. Optional reductive removal of -SAc with Ra-Ni gives the corresponding 2'-deoxy-beta-disaccharides. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.08.063

文献信息

• Efficient Preparation of 2‐SAc‐Glycosyl Donors and Investigation of Their Application in the Synthesis of 2‐Deoxyglycosides
  作者：Tao Luo、Qiang Zhang、Yang‐Fan Guo、Zhi‐Chao Pei、Hai Dong

  DOI：10.1002/ejoc.202200533

  日期：2022.7.14

  We have developed efficient strategies for the synthesis of glycosyl donors with 2-thioacetyl (SAc) groups in order to synthesize 2-deoxysugars with absolute α/β configuration.

  我们开发了合成具有 2-硫乙酰 (SAc) 基团的糖基供体的有效策略，以合成具有绝对 α/β 构型的 2-脱氧糖。
• A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light To Synthesize Deoxyglycosides
  作者：Jian-Tao Ge、Lang Zhou、Tao Luo、Jian Lv、Hai Dong

  DOI：10.1021/acs.orglett.9b02033

  日期：2019.8.2

  We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by desulfurization under UV light for 1-2 h in the presence of TCEP center dot HCl. The method was then used to synthesize 2-deoxy glycosides with absolute alpha/beta-configuration via stereoselective control of C-2 thioacetate in glycosylation.