Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside | 136773-79-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside
• CAS: 136773-79-0
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: ZSSWHJUQNUJYIC-AQGHMYMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.17
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 在 三氯化铝 、 三氟甲磺酸三甲基硅酯 、 硼烷-三甲胺络合物 、 4 A molecular sieve 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.67h， 生成
  参考文献：
  名称：

  异蒜素的合成

  摘要：

  已经通过消旋异源别甲唑啉衍生物的区域选择性糖苷化与二糖三氯乙酰胺酸盐的收敛选择性方法，合成了异蒜胺素，一种新型的几丁质酶抑制剂。

  DOI：

  10.1039/c39910001099
• 作为产物：
  描述：

  Allyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside 在 sodium hydroxide 作用下， 反应 144.0h， 以100%的产率得到Allyl 2-Amino-4,6-O-benzylidene-2-deoxy-α-D-allopyranoside
  参考文献：
  名称：

  异蒜素的合成

  摘要：

  已经通过消旋异源别甲唑啉衍生物的区域选择性糖苷化与二糖三氯乙酰胺酸盐的收敛选择性方法，合成了异蒜胺素，一种新型的几丁质酶抑制剂。

  DOI：

  10.1039/c39910001099

文献信息

• Convenient Synthesis of 2-Azido-2-deoxy-aldoses by Diazo Transfer
  作者：Andrea Vasella、Christian Witzig、Jose-Luis Chiara、Manuel Martin-Lomas

  DOI：10.1002/hlca.19910740842

  日期：1991.12.11

  trifluoromethanesulfonyl azide (TfN3) to 2-amino-2-deoxy-glycoses constitutes a high-yielding, simple procedure for the preparation of partially protected or unprotected 2-azido-2-deoxy-aldoses. Thus, the D-allosamine derivative 2 gave 93% of 3, while diazo transfer to D-glucosamine, D-mannosamine, and D-galactosamine, followed by acetylation, yielded the azides 5, 7, and 9 in yields of 74–91, 65, and 70%, respectively

  重氮从三氟甲磺酰基叠氮化物（TfN 3）转移至2-氨基-2-脱氧葡萄糖构成了制备部分保护或未保护的2-叠氮基2-脱氧醛糖的高产率，简单方法。因此，d-allosamine衍生物2得到的93％3，而重氮基转移到d葡糖胺，d甘露糖胺，和d半乳糖胺，随后通过乙酰化，得到叠氮化物5，7，和9中的74-91的产率，分别为65％和70％。
• Versatile and self-assembling urea-linked neosaccharides from sugar aminoalcohols
  作者：Emiliano Bedini、Luigi Cirillo、Michelangelo Parrilli

  DOI：10.1016/j.tet.2012.12.005

  日期：2013.1

  The increasing interest in urea compounds as self-assembling molecules, ion transporters and organo-catalysts prompted several efforts towards synthetic urea-linked glycomimetics. In this frame we studied in details a novel two steps dimerization reaction of sugar vicinal aminoalcohol building blocks, opening a synthetic path to a series of urea-linked neosaccharides. Glucosamine neodisaccharide possessing an oxazolidinone-urea-oxazolidinone system could be transformed into both cyclic and higher linear neosaccharides. Furthermore, a series of six urea-linked glucosamine and galactosamine neodisaccharides was tested for self-assembling properties by measuring NMR spectra at different temperatures and concentrations as well as by gelation of several organic solvents. (c) 2012 Elsevier Ltd. All rights reserved.
• Synthesis ofN-Acetylallosamine-Derived Disaccharides
  作者：Jean-Luc Maloisel、Andrea Vasella

  DOI：10.1002/hlca.19920750505

  日期：1992.8.13

  AbstractThe protected disaccharide 44, a precursor for the synthesis of allosamidin, was prepared from the glycosyl acceptor 8 and the donors 26–28, best yields being obtained with the trichloroacetimidate 28 (Scheme 6). Glycosidation of 8 or of 32 by the triacetylated, less reactive donors 38–40 gave the disaccharides 46 and 45, respectively, in lower yields (Scheme 7). Regioselective glycosidation of the diol 35 by the donors 38–40 gave 42, the axial, intramolecularly H‐bonded OHC(3) group reacting exclusively (Scheme 5). The glycosyl acceptor 8 was prepared from 9 by reductive opening of the dioxolane ring (Scheme 3). The donors 26–28 were prepared from the same precursor 9 via the hemiacetal 25. To obtain 9, the known 10 was de‐N‐acetylated (→ 18), treated with phthalic anhydride (→ 19), and benzylated, leading to 9 and 23 (Schemes 2 and 3). Saponification of 23, followed by acetylation also gave 9. Depending upon the conditions, acetylation of 19 yielded a mixture of 20 and 21 or exclusively 20. Deacetylation of 20 led to the hydroxyphthalamide 22. De‐N‐acetylation of the 3‐O‐benzylated β‐D‐glycosides 11 and 15, which were both obtained from 10, was very sluggish and accompanied by partial reduction of the O‐allyl to an O‐propyl group (Scheme 2). The β‐D‐glycoside 30 behaved very similarly to 11 and 15. Reductive ring opening of 31, derived from 29, yielded the 3‐O‐acetylated acceptor 32, while the analogous reaction of the β‐D‐anomer 20 was accompanied by a rapid 3‐O→4‐O acyl migration (→34; Scheme 4). Reductive ring opening of 21 gave the diol 35. The triacetylated donors 38–40 were obtained from 20 by debenzylidenation, acetylation (→36), and deallylation (→37), followed by either acetylation (→38), treatment with Me3SiSEt (→39), or Cl3CCN (→ 40).