O-(2,3,4-tri-O-benzoyl-α-D-glucopyranosyl)-(1<*>1)-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside | 146530-69-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4-tri-O-benzoyl-α-D-glucopyranosyl)-(1<*>1)-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-[(2R,3R,4S,5R,6R)-3,4,5-tribenzoyloxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 146530-69-0
• 化学式: C₆₁H₅₀O₁₈
• 分子量: 1071.06
• InChiKey: QHCLEAYXSMBNTF-JHOJVHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  79
• 可旋转键数：
  25
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-tri-O-benzoyl-α-D-glucopyranosyl)-(1<*>1)-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 乙腈 为溶剂， 反应 12.5h， 生成 6-deoxy-α,α-D-trehalose
  参考文献：
  名称：

  单和双脱氧α，α-海藻糖类似物的合成

  摘要：

  摘要在本文中，我们描述了α，α-d-海藻糖的四个单脱氧和四个双脱氧类似物的合成和NMR表征。对称的（2,2'-，3,3'-，4,4'-和6,6'-）双脱氧类似物是通过选择性保护和随后的所需羟基组的自由基脱氧而获得的。通过α，α-海藻糖的脱对称和随后在自由基条件下的脱氧合成不对称的（2'-，3'-，4'-和6'-）单脱氧类似物。通过广泛使用2D {1 H，1 H}和{1 H，13 C}相关NMR实验，可以实现这些脱氧海藻糖光谱中所有1 H和13 C共振的完全分配。

  DOI：

  10.1016/j.carres.2007.05.009
• 作为产物：
  描述：

  6,6'-di-O-tert-butyldimethylsilyl-2,3,4,2',3',4'-hexa-O-benzoyl-α,α-D-trehalose 在 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 吡啶 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 O-(2,3,4-tri-O-benzoyl-α-D-glucopyranosyl)-(1<*>1)-2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside
  参考文献：
  名称：

  单和双脱氧α，α-海藻糖类似物的合成

  摘要：

  摘要在本文中，我们描述了α，α-d-海藻糖的四个单脱氧和四个双脱氧类似物的合成和NMR表征。对称的（2,2'-，3,3'-，4,4'-和6,6'-）双脱氧类似物是通过选择性保护和随后的所需羟基组的自由基脱氧而获得的。通过α，α-海藻糖的脱对称和随后在自由基条件下的脱氧合成不对称的（2'-，3'-，4'-和6'-）单脱氧类似物。通过广泛使用2D {1 H，1 H}和{1 H，13 C}相关NMR实验，可以实现这些脱氧海藻糖光谱中所有1 H和13 C共振的完全分配。

  DOI：

  10.1016/j.carres.2007.05.009

文献信息

• Use of Diphenylacetyl Chloride as Protective Reagent for Sugars
  作者：F. Santoyo-González、F. García-Calvo-Flores、J. Isac-García、R. Robles-Diaz、A. Vargas-Berenguel

  DOI：10.1055/s-1994-25413

  日期：——

  Diphenylacetyl chloride is used as a protective reagent for methyl α-D-glucopyranoside, methyl α-D-mannopyranoside, and α,α-trehalose showing a good regioselectivity. The obtained diphenylacetyl esters were readily removed under neutral and mild conditions with N-bromosuccinimide followed by thiourea, in a one-pot reaction, in the presence of acetyl or benzoyl groups.

  二苯基乙酰氯被用作甲基δ-D-吡喃葡萄糖苷、甲基δ-D-吡喃甘露糖苷和δ,δ-曲哈洛糖的保护试剂，具有良好的区域选择性。在乙酰基或苯甲酰基存在的中性温和条件下，用 N-溴代丁二酰亚胺，然后用硫脲进行单锅反应，很容易除去得到的二苯基乙酰酯。
• Synthetic studies toward pyruvate acetal containing saccharides. Synthesis of the carbohydrate part of the Mycobacterium smegmatis pentasaccharide glycolipid and fragments thereof for the preparation of neoantigens
  作者：Thomas Ziegler、Elisabeth Eckhardt、Veronique Birault

  DOI：10.1021/jo00057a021

  日期：1993.2

  A series of 2,3-di-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-D-glucopyranosyl donors (beta-phenylthio 3, bromide 4, alpha-chloride 5, beta-fluoride 6, and trichloroacetimidate 7) were prepared from the corresponding alpha-allyl glucoside 1 via the deallylated glucose 2 and were tested in glycosylation reactions with methanol to give the pyruvylated methyl glucosides 8 and 9 and with methyl 2,4,6-tri-O-benzoyl-beta-D-glucopyranoside 10 to give the disaccharide 11. Best results with respect to yield and beta-selectivity of the coupling were achieved with imidate 7. Thus, the 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-3-O-methyl-D-glucopyranosyl trichloroacetimidate 14 was prepared from its benzyl glucoside 12 and used for the synthesis of fragments related to the Mycobacterium smegmatis lipopentasaccharide. Trimethylsilyl trifluoromethanesulfonate-mediated condensation of 14, 5-[(benzyloxycarbonyl)amino]pentanol, and 10, respectively, followed by deblocking of the products 15 and 17 gave the pyruvylated aminopentyl glucoside 16 and methyl laminaribioside 18. Treatment of 17 with dichloromethyl methyl ether gave the laminaribiosyl chloride 19, coupling of which with protected 5-aminopentanol gave 20 also obtained from 14 and the monosaccharide nucleophile 26. The trisaccharide 5-aminopentyl glycoside fragment 42 was prepared by first coupling of 14 and benzyl 2-O-benzoyl-4,6-O-[(S)-1-(methoxycarbonyl)ethylidene]-alpha-D-glucopyranoside 30 that was converted to the bispyruvylated laminaribiose imidate 33, followed by condensation with thioglycoside 38 obtainable in four steps from 1,2,4,6-tetra-O-acetyl-3-O-benzyl-beta-D-glucopyranose to give the trisaccharide ethyl thioglycoside 40. Next, NIS-mediated condensation of 40 and 5-[(benzyloxycarbonyl)amino]pentanol followed by deblocking gave 42. Pentasaccharide 45 was similarly prepared from 40 and hepta-O-benzoyltrehalose 43 to give first the blocked saccharide 44, deblocking of which afforded the target pentasaccharide.
• Synthesis of mono- and dideoxygenated α,α-trehalose analogs
  作者：Fiona L. Lin、Herman van Halbeek、Carolyn R. Bertozzi

  DOI：10.1016/j.carres.2007.05.009

  日期：2007.10

  the synthesis and NMR characterization of four mono- and four dideoxygenated analogs of α,α- d -trehalose. The symmetrical (2,2′-, 3,3′-, 4,4′- and 6,6′-) dideoxy analogs were obtained via selective protection and subsequent radical deoxygenation of the desired hydroxyl group set. The unsymmetrical (2′-, 3′-, 4′- and 6′-) monodeoxy analogs were synthesized by desymmetrization of α,α-trehalose and subsequent

  摘要在本文中，我们描述了α，α-d-海藻糖的四个单脱氧和四个双脱氧类似物的合成和NMR表征。对称的（2,2'-，3,3'-，4,4'-和6,6'-）双脱氧类似物是通过选择性保护和随后的所需羟基组的自由基脱氧而获得的。通过α，α-海藻糖的脱对称和随后在自由基条件下的脱氧合成不对称的（2'-，3'-，4'-和6'-）单脱氧类似物。通过广泛使用2D 1 H，1 H}和1 H，13 C}相关NMR实验，可以实现这些脱氧海藻糖光谱中所有1 H和13 C共振的完全分配。