(S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoate | 77870-91-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoate
• 英文别名: N-(benzyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-serine methyl ester；N-benzyloxycarbonyl-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-serine methyl ester；O-[2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl]-N-carbobenzyloxy-L-serine methyl ester；methyl (2S)-2-(phenylmethoxycarbonylamino)-3-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoate
• CAS: 77870-91-8
• 化学式: C₄₆H₄₉NO₁₀
• 分子量: 775.896
• InChiKey: CDZSXCDCDDJFRH-KNEQNCEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  57
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-四苄基-D-吡喃葡萄糖 在 正丁基锂 、 silver perchlorate 作用下， 以 苯 为溶剂， 反应 25.5h， 生成 (S)-2-((benzyloxycarbonyl)amino)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)propanoate
  参考文献：
  名称：

  GLUCOSYLATION USING GLUCOPYRANOSYL DIMETHYLPHOSPHINOTHIOATE

  摘要：

  在过氯酸银存在的情况下，从2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基二甲基硫代膦酸酯和醇类中制备了几种葡萄糖苷，且收率良好。通过这种方法，主要获得了α-葡萄糖苷。

  DOI：

  10.1246/cl.1985.297

文献信息

• AuCl₃- and AuCl₃-Phenylacetylene-Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates
  作者：Rashmi Roy、Ashok Kumar Palanivel、Asadulla Mallick、Yashwant D. Vankar

  DOI：10.1002/ejoc.201500137

  日期：2015.6

  obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.

  通过使用 AuCl3-苯乙炔中继催化剂体系进行武装和解除武装的三氯乙酰亚胺基糖基供体的糖基化。该催化体系的有效性也与单独使用 作为催化剂的有效性进行了比较。使用这些催化剂的糖基化在室温下在 5-45 分钟内有效进行。2-O-乙酰保护的去武装糖基供体的糖基化获得了优异的非对映选择性，而武装糖基三氯乙酰亚胺产生了异头糖苷的混合物。酸敏感性亲核试剂，如 Fmoc-丝氨酸叔丁酯或 Fmoc-苏氨酸叔丁酯，在室温温和条件下成功地进行了糖基化，尽管产率适中。
• Glycosyldisulfides: a new class of solution and solid phase glycosyl donors
  作者：Benjamin G. Davis、Sarah J. Ward、Phillip M. Rendle

  DOI：10.1039/b008734n

  日期：——

  Mixed glycosyl disulfides are not only glycomimetics but also glycosyl donors that may be readily constructed in either armed ether-protected or disarmed ester-protected and in soluble or solid-supported forms from corresponding glycosyl methanethiosulfonates and used in the glycosylation of a variety of representative acceptors.

  混合糖基二硫化物不仅是糖模拟物，而且是糖基供体，可以很容易地以武装醚保护或解除武装酯保护的形式构建，并以相应的糖基甲硫代磺酸盐以可溶或固体支持的形式构建，并用于各种代表性受体的糖基化.
• Stereoselective O-glycosylation reactions using glycosyl donors with diphenylphosphinate and propane-1,3-diyl phosphate leaving groups
  作者：Hariprasad Vankayalapati、Gurdial Singh、Isabelle Tranoy

  DOI：10.1016/s0957-4166(01)00227-0

  日期：2001.6

  Glycosyl donors having a diphenylphosphinate and a propane-1,3-diyl phosphate leaving group were easily prepared by the addition of the anomeric hydroxyl group of 2,3,4,6-tetra-O-benzyl-α,β-d-glucopyranose to diphenylphosphinic and propane-1,3-diyldioxyphosphoryl chlorides. These glycosyl donors were selectively glycosylated with a number of primary and secondary oxygen nucleophiles in the presence

  通过添加2,3,4,6-四-O-苄基-α，β-d-吡喃葡萄糖的异头羟基可以轻松制备具有二苯基次膦酸酯和丙烷1,3-二苯基磷酸酯离去基团的糖基供体生成二苯基次膦酸和丙烷1，，3-二基二氧基磷酰氯。在三甲基甲硅烷基三氟甲磺酸酯（TMSOTf）存在下，这些糖基供体被许多伯和仲氧亲核试剂选择性糖基化。磷酸1，3-二烷基酯的使用导致β- O-连接的糖苷的立体选择性形成。
• Direct Dehydrative Glycosylation Catalyzed by Diphenylammonium Triflate
  作者：Mei-Yuan Hsu、Sarah Lam、Chia-Hui Wu、Mei-Huei Lin、Su-Ching Lin、Cheng-Chung Wang

  DOI：10.3390/molecules25051103

  日期：——

  dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

  描述了在微波辐射下由三氟甲磺酸二苯基铵催化的碳水化合物半缩醛的直接脱水糖基化的方法。武装和解除武装的糖基-C1-半缩醛供体均以中等至优异的产率有效糖基化，无需任何干燥剂和化学计量添加剂。该方法已成功应用于固相糖基化。
• Improved catalytic and stereoselective glycosylation with glycosyl N-trichloroacetylcarbamate: application to various 1-hydroxy sugars
  作者：Tatsuya Shirahata、Jun-ichi Matsuo、Satoko Teruya、Nozomu Hirata、Taku Kurimoto、Nanao Akimoto、Toshiaki Sunazuka、Eisuke Kaji、Satoshi Ōmura

  DOI：10.1016/j.carres.2010.01.011

  日期：2010.4

  Efficient catalytic and stereoselective glycosylation was achieved by activating a glycosyl N-trichloroacetylcarbamate with a catalytic amount of Lewis acid in the presence of a glycosyl acceptor and 5A molecular sieves. Catalytic one-pot dehydrative glycosylation of a 1-hydroxy carbohydrate was achieved stereoselectively by reaction with trichloroacetyl isocyanate, followed by activation with a catalytic

  在存在糖基受体和5A分子筛的情况下，通过用催化量的路易斯酸活化N-三氯乙酰氨基甲酸糖基，可以实现有效的催化和立体选择性糖基化。通过与三氯乙酰基异氰酸酯反应，然后用催化量的活化剂活化，选择性地实现了1-羟基碳水化合物的催化一锅脱水糖基化反应。