benzyl 2,3-di-O-benzyl-β-D-glucopyranoside | 67831-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-di-O-benzyl-β-D-glucopyranoside
• 英文别名: Benzyl 2,3-di-O-benzyl-beta-D-glucopyranoside；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-4,5,6-tris(phenylmethoxy)oxan-3-ol
• CAS: 67831-41-8
• 化学式: C₂₇H₃₀O₆
• 分子量: 450.532
• InChiKey: LSHLWIIYISYWAF-IURCNINISA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  615.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-di-O-benzyl-β-D-glucopyranoside 在 盐酸 、 氧气 、 碳酸氢钠 、 铂 作用下， 生成 O¹,O²,O³-tribenzyl-β-D-glucopyranuronic acid methyl ester
  参考文献：
  名称：

  �ber 4-Methyl-glucurons�ure

  摘要：

  DOI：

  10.1007/bf00903021
• 作为产物：
  描述：

  苄基 alpha-D-吡喃葡萄糖苷 在 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 benzyl 2,3-di-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of β-d-Gluco-, α-l-Ido-, and α-l-Altropyranosiduronic Acids from Δ⁴-Uronates

  摘要：

  The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using boranetetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the C-1(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.

  DOI：

  10.1021/jo981477k

文献信息

• In situ Activating Glycosylation of 6-Deoxysugars: Synthesis of<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-Fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-quinovosyl-(1→4)-<b>D</b>-quinovose
  作者：Shinkiti Koto、Ami Kusunoki、Motoko Hirooka

  DOI：10.1246/bcsj.73.967

  日期：2000.4

  The linear tetrasaccharide, α-D-fucopyranosyl-(1→4)-α-D-fucopyranosyl-(1→4)-α-D-quinovopyranosyl-(1→4)-D-quinovopyranose, the sugar cluster of asterosaponin A from the starfish, Asterias amurensis, was synthesized in a convergent manner. We employed an in situ activating glycosylation using 1-OH sugar derivatives and a system of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine as well as a related system.

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。
• β-Acarbose. II. The Preparation of Various Carbohydrate Trifluoromethanesulfonates
  作者：Joseph C. McAuliffe、Robert V. Stick

  DOI：10.1071/c96152

  日期：——

  Three carbohydrate trifluoromethanesulfonates, of potential use in the alkylation of a 1-epivalienamine derivative to produce precursors of β-acarbose, have been prepared from the appropriate alcohols. The conversion of two of these trifluoromethanesulfonates into the primary amine, via the corresponding azide, is also reported.

  三种可能用于 1-环戊二烯胺衍生物烷基化的碳水化合物三氟甲磺酸盐 1-epivalienamine 衍生物的烷基化过程中，生成 β-arbose 的前体。 β-阿卡波糖的前体。这些 其中两种三氟甲磺酸盐通过相应的叠氮化物转化为伯胺、 还报道了通过相应叠氮化物将其中两种三氟甲磺酸酯转化为伯胺的过程。
• Oxidative esterification of primary alcohols with TEMPO/CaCl 2 /Oxone under hydrous conditions
  作者：Sven Hackbusch、Andreas H. Franz

  DOI：10.1016/j.tetlet.2016.05.066

  日期：2016.6

  Symmetric esters are important compounds in the chemical industry, which creates demand for simple and efficient synthetic routes. Oxidative esterification is a promising method to achieve these aims. Here, we show that TEMPO/CaCl2/Oxone forms a convenient catalytic system for the synthesis of the aforementioned symmetric esters from primary alcohols in a biphasic dichloromethane–water solvent mixture. The

  对称酯是化学工业中的重要化合物，这对简单有效的合成路线产生了需求。氧化酯化是实现这些目标的一种有前途的方法。在这里，我们表明TEMPO / CaCl 2 / Oxone形成了便捷的催化体系，用于在双相二氯甲烷-水溶剂混合物中由伯醇合成上述对称酯。反应方法的底物范围与先前公开的方法互补，并且末端氧化剂似乎起重要作用。另外，已表明该方法比醇官能团优先氧化硫醇，得到二硫键桥接的化合物。
• Total synthesis of the mollu-series glycosyl ceramides α-d-Manp-(1→3)-β-d-Manp-(1→4)-β-d-Glcp-(1→1)-Cer and α-d-Manp-(1→3)-[β-d-Xylp-(1→2)]-β-d-Manp-(1→4)-β-d-Glcp-(1→1)-Cer
  作者：Masato Mori、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(90)84167-s

  日期：1990.1

  Abstract The mollu-series glycosphingolipids, O-α- d -mannopyranosyl-(1→3)-O-β- d -mannopyranosyl-(1→4)-O-β- d -glucopyranosyl - (1→1)-2-N-tetracosanoyl-(4E)-sphingenine and O-α- d -mannopyranosyl-(1→3)-O-[β- d -xylopyranosyl-(1→2)]-O-β- d -mannopyranosyl-(1→4) -O-β- d -glucopyranosyl-(1→1)-2-N-tetracosanoyl-(4E)-sphingenine, were synthesized for the first time by using 2,3,4-tri-O-acetyl- d -xylopyranosyl

  摘要软体动物系列糖鞘脂，O-α-d-甘露吡喃糖基-（1→3）-O-β-d-甘露吡喃糖基-（1→4）-O-β-d-吡喃葡萄糖基-（1→1）-2 -N-十四烷酰基-（4E）-鞘氨醇和O-α-d-甘露吡喃糖基-（1→3）-O- [β-d-吡喃吡喃糖基-（1→2）]-O-β-d-甘露吡喃糖基-（利用2,3,4-三-O-乙酰基首次合成了1→4）-O-β-d-吡喃葡萄糖基-（1→1）-2-N-十四烷酰基-（4E）-鞘氨醇-d-木吡喃糖基三氯乙酰亚胺酸酯，甲基2,3,4,6-四-O-乙酰基-1-硫代-α-d-甘露吡喃糖苷，苄基O-（4,6-二-O-苄基-β-d-甘露吡喃糖基）-（1→4）-2,3,6-三-O-苄基-β-d-吡喃葡萄糖苷9和（2S，3R，4E）-2-叠氮基-3-O-（叔丁基二苯基甲硅烷基）-以4-十八碳烯-1,3-二醇6为主要中间体。六-O-苄基二糖9是通过偶联两个2,3-二-O-烯丙基-
• Klemer, Chemische Berichte, 1959, vol. 92, p. 218,222
  作者：Klemer

  DOI：——

  日期：——