methyl 2,3-di-O-benzyl-6-O-trityl-α-D-galactopyranoside | 71756-38-2

• 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: methyl 2,3-di-O-benzyl-6-O-trityl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(trityloxymethyl)oxan-3-ol
• CAS: 71756-38-2
• 化学式: C₄₀H₄₀O₆
• 分子量: 616.754
• InChiKey: GZWDCFUAYQOXTM-CHXCTFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  46
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-O-trityl-α-D-galactopyranoside 在 吡啶 、 盐酸 、 sodium azide 、 硫酸 、 四乙基氯化铵 、 溶剂黄146 、 三丁基氧化锡 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.67h， 生成 1,4-diazido-1,4-dideoxy-2-O-(4'-azido-2',3'-di-O-benzyl-4'-deoxy-6'-O-propionyl-α-D-glucopyranosyl)-D-glucitol
  参考文献：
  名称：

  山梨素A 1和位置异构体的全合成

  摘要：

  首次以区域和立体控制的方式描述了山梨素A 1（1）和位置异构体（7）的全合成。

  DOI：

  10.1016/0040-4020(80)80148-7
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)tetrahydro-6-methoxy-2-((trityloxy)methyl)-2H-pyran-3-ol 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl 2,3-di-O-benzyl-6-O-trityl-α-D-galactopyranoside
  参考文献：
  名称：

  Studies of the stereoselective reduction of ketosugar (hexosulose)

  摘要：

  The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported, Combining Our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars, These findings are valuable in the synthesis of various carbohydrate derivatives. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01472-1

文献信息

• Synthesis of methyl derivatives of uronic acids. I. Synthesis of methyl (methylα-D-galactopyranosid)uronate and its 2-, 3-, and 4-O-methyl ethers
  作者：V. I. Grishkovets、A. E. Zemlyakov、V. Ya. Chirva

  DOI：10.1007/bf00580445

  日期：1982.5

  Alternative unidirectional methods for synthesizing methyl (methyl α-D-galactopyranosid)uronate and its mono-O-methyl ethers by the oxidation (with CrO3-H2SO4-acetone) of the corresponding methyl O-benzyl-O-methyl-α-D-galactopyranosides having unsubstituted 6-OH groups to the corresponding methyl O-benzyl-O-methyl-α-D-galactouronic acids followed by esterification with CH2N2 and the catalytic hydrogenolysis

  通过相应的甲基 O-苄基-O-甲基-α-D-氧化（用 CrO3-H2SO4-丙酮）合成（甲基 α-D-吡喃半乳糖苷）糖醛酸甲酯及其单-O-甲基醚的替代单向方法提出了具有未取代的 6-OH 基团的吡喃半乳糖苷与相应的甲基 O-苄基-O-甲基-α-D-半乳糖醛酸，然后用 CH2N2 酯化和苄基的催化氢解。
• Novel pyranosyl cytosines: pharmaceutical formulations and methods
  申请人：——

  公开号：US20030216575A1

  公开（公告）日：2003-11-20

  This invention is directed to novel pyranosyl cytosine compounds depicted graphically as structure I. This invention is further directed to a unique methodology for their preparation using solid-phase methodology. These hexopyranosyl cytosine derived natural product analogs share their parent compounds broad-spectrum antimicrobial and anti-fungal profile and represent a vast, novel compound class of 50S rRNA directed inhibitors of protein translation. 1

  这项发明涉及以图示结构I形式表示的新型吡喃基胞嘧啶化合物。该发明进一步涉及一种独特的固相方法用于它们的制备。这些以己糖基胞嘧啶为基础的天然产物类似物与它们的母体化合物共享广谱抗微生物和抗真菌特性，并代表了一类广泛的、新型的50S rRNA定向蛋白翻译抑制剂化合物。
• Action du N-bromosuccinimide sur les dioxolannes en série bicyclo [2.2.1 ]heptanique. Limitation des transpositions de wagner-meerwein
  作者：Akram Bazbouz、Henri Christol、Jacques Coste、Françoise Plenat

  DOI：10.1016/0040-4020(80)80151-7

  日期：1980.1

  Vicinal benzoyloxy-trans-bicyclo [2.2.1] heptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton. The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable

  N-溴丁二酰亚胺和带有2-芳基-1,3-二氧戊环骨架的降冰片烷形成了否则难以获得的邻苯甲酰氧基-反式-双环[2.2.1]庚烷溴代醇。中间体二氧杂环丁烷离子的更高稳定性降低了瓦格纳-梅尔温重排和邻位氯参与的趋势，这是在涉及到稳定性较差的中间体时通常观察到的过程。然而，甲氧基羰基邻基的参与和瓦格纳·梅尔温重排分别发生在甲氧基羰基双环[2.2.1]庚烷和硼烷化合物中。
• Studies of the stereoselective reduction of ketosugar (hexosulose)
  作者：Cheng-Wei Tom Chang、Yu Hui、Bryan Elchert

  DOI：10.1016/s0040-4039(01)01472-1

  日期：2001.10

  The results from the studies of the stereoselective reduction of ketosugar (hexosulose) were reported, Combining Our results and those reported in the literature, we summarize the factors in controlling the stereoselective reduction of ketosugars, These findings are valuable in the synthesis of various carbohydrate derivatives. (C) 2001 Published by Elsevier Science Ltd.
• Total synthesis of sorbistin A1 and a positional isomer
  作者：Tomoya Ogawa、Kiyoaki Katano、Masanao Matsui

  DOI：10.1016/0040-4020(80)80148-7

  日期：1980.1

  Total synthesis of sorbistin A1 (1) and a positional isomer (7) is described for the first time in a regio- and stereo-controlled manner.

  首次以区域和立体控制的方式描述了山梨素A 1（1）和位置异构体（7）的全合成。