1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-galactopyranose | 160584-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-galactopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)-2-(1,3-thiazol-2-yl)oxan-2-yl] acetate
• CAS: 160584-12-3
• 化学式: C₃₉H₃₉NO₇S
• 分子量: 665.807
• InChiKey: BMZVVODHPNSVPG-LZEMFQRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-galactopyranose 在 三氟甲磺酸三甲基硅酯 、 叠氮基三甲基硅烷 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到azido 2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-α-D-galactopyranoside
  参考文献：
  名称：

  A General Synthetic Route to Anomeric .alpha.-Azido and .alpha.-Amino Acids and Formal Synthesis of (+)-Hidantocidin

  摘要：

  DOI：

  10.1021/jo00103a057
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-D-吡喃半乳糖 在 正丁基锂 、 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.58h， 生成 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-galactopyranose
  参考文献：
  名称：

  Thiazole-Based Synthesis of Formyl C-Glycosides

  摘要：

  A method for the installation of the formyl group at the anomeric position of pyranoses and furanoses starting from the corresponding lactones has been developed. The strategy involves the addition of 2-lithiothiazole to the sugar lactone, followed by the silane reduction of the acetylated resultant ketol and the unmasking of the formyl group from the thiazole ring. All steps have been studied in some details to improve chemical efficiency and stereochemical control. Hence, reversed alpha:beta ratios of ketols were found in kinetic and thermodynamic mixtures, the former being consistent with a steric effect control of the substituents and the latter by the electronic effect of the ring oxygen. Seven sugar aldehydes with different D-pyranosidic (2,3,4,6-tetra-O-benzyl-gluco, -galacto, and -manno, 2-azido-3,4,6-tri-O-benzyl-2-deoxy-galacto) and D-furanosidic moieties (5-O-benzyl-2,3-isopropylidene-ribo; 2,3,5-tri-O-benzyl-ribo; 2,3:5,6-di-O-isopropylidene-manno) were prepared in 52-65% isolated overall yield from the corresponding lactone.

  DOI：

  10.1021/jo00100a050

文献信息

• Thiazolylketol acetates as glycosyl donors. Stereoselective synthesis of α-linked ketodisaccharides
  作者：Alessandro Dondoni、Alberto Marra、Isabel Rojo、Marie-Christine Scherrmann

  DOI：10.1016/0040-4020(95)01095-5

  日期：1996.2

  TMSOTf-promoted glycosidation of acetate (α)-2 and acetate 7 donors with 1 equiv of primary 3 and secondary 5 sugar alcohols acceptors gave exclusively the corresponding α-d-ketodisaccharides 4a, 8a, 11a, and 12a in 60–73% yield. On the other hand glycosidation of the acetate 6 with the primary alcohol 3 under the above conditions afforded a mixture of α- and β-d-ketodisaccharides 9a and 10a in ca

  TMSOTf促进的乙酸盐（α）-2和乙酸盐7供体与1当量的伯3和仲5糖醇受体的糖基化，以60-73％的收率仅产生相应的α-d-酮二糖4a，8a，11a和12a。另一方面，在上述条件下，乙酸6与伯醇3的糖基化得到α-和β-d-酮二糖9a和10a的混合物。在约。1：1的比例。通过与带有甲基，羧甲基和2-呋喃基的酮糖进行比较，指出了噻唑环对于这些酮醇乙酸酯的容易糖基化的重要作用。将噻唑基至甲酰基的解封反应序列应用于噻唑基酮二糖，得到相应的醛，其分别通过还原和氧化转化为醇和酯。