3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose | 138902-22-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
• 英文别名: 1,2:5,6-Di-O-isopropylidene-3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-α-D-glucofuranose；1,2:5,6-di-O-isopropylidene-α-D-glucofuranos-3-yl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranose；(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 138902-22-4
• 化学式: C₄₆H₅₄O₁₁
• 分子量: 782.928
• InChiKey: OIGCVNUVBSVJER-XNHKFZGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-galactopyranosyl methanethiosulfonate 在 4 A molecular sieve 、 DMTST 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-(1-3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Glycosyl Disulfides:  Novel Glycosylating Reagents with Flexible Aglycon Alteration

  摘要：

  Glycosyl disulfides have been shown for the first time to be effective glycosyl donors. Glucosylation and galactosylation of a panel of representative alcohol acceptors allowed the formation of 28simple glycosides, disaccharides, and glycoamino acids in yields of up to 90%. As well as providing a novel class of effective glycosyl donors, the ability to easily alter the nature of the aglycon and the ability to differently activate donors that differ only in their aglycon simply through altering conditions lends glycosyl disulfide donors to their use in latent-active reactivity tuning Strategies,.

  DOI：

  10.1021/jo051374j

文献信息

• Glycosyl iodides are highly efficient donors under neutral conditions
  作者：Michael J. Hadd、Jacquelyn Gervay

  DOI：10.1016/s0008-6215(99)00146-9

  日期：1999.7

  Abstract Glycosyl iodides have been prepared and subjected to glycosylation under neutral conditions. The reactions are highly efficient, giving α glycosides even with sterically demanding glycosyl acceptors. Glucosyl iodides react with allyl alcohol slowest and require refluxing conditions. Galactosyl iodides are intermediate in reactivity, providing the allyl glycoside in 3 h at room temperature

  摘要制备了糖基碘化物并在中性条件下进行糖基化。该反应是高效的，即使具有空间上要求的糖基受体也能得到α糖苷。葡萄糖基碘与烯丙醇的反应最慢，需要回流条件。半乳糖基碘化物是反应性的中间产物，在室温下3小时内可提供烯丙基糖苷，而岩藻糖基碘化物的糖基化在相似条件下可在不到1小时内发生。用包括异头羟基在内的各种受体证明了反应的范围和局限性，得到了海藻糖类似物。在不存在C-2参与的情况下，只需将溶剂从苯改成乙腈就可以实现葡萄糖基碘化物的β-选择性糖基化。
• Tsvetkov, Yury E.; Klotz, Wolfgang; Schmidt, Richard R., Liebigs Annalen der Chemie, 1992, # 4, p. 371 - 376
  作者：Tsvetkov, Yury E.、Klotz, Wolfgang、Schmidt, Richard R.

  DOI：——

  日期：——
• Dichloro‐cyanoacetimidates as Glycosyl Donors
  作者：Uwe Schmelzer、Zhaojun Zhang、Richard R. Schmidt

  DOI：10.1080/07328300701410650

  日期：2007.6.1

  Transformation of 1-O-unprotected glucose and galactose derivatives (1a-d) into O-glycosyl dichloro-cyanoacetimidates (2a-d) was performed with dichloro-cyanoacetonitrile in the presence of DBU as base. Reaction with different acceptors (3a-d) under TMSOTf catalysis afforded glycosides 4 in high yields. Competition experiments with O-glucopyranosyl trichloroacetimidate 10a, bearing a 4-tert-butylbenzyl group at 6-O, and O-glucopyranosyl dichloro-cyanoacetimidate 10b, bearing a 4-methylbenzyl group at 6-O, displayed similar reactivities for these two types of glycosyl donors.