6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose | 729596-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
• 英文别名: 6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose；6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-D-glycero-α-D-gluco-heptofuranose；benzyl N-[(1R,2R)-1-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,3-dihydroxypropan-2-yl]carbamate
• CAS: 729596-19-4
• 化学式: C₁₈H₂₅NO₈
• 分子量: 383.398
• InChiKey: NJUBQALBEREUSK-BKQXGZDCSA-N

物化性质

• 熔点：
  135-137 °C
• 沸点：
  641.2±55.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose 在 palladium on activated charcoal 盐酸 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 水 为溶剂， 25.0 ℃ 、551.58 kPa 条件下， 反应 26.5h， 生成 1,6-dideoxy-1,6-imino-(2S,3R,4R,5R,6R)-L-glycero-D-gluco-heptitol hydrochloride
  参考文献：
  名称：

  d-葡萄糖衍生的α，β-不饱和酯的不对称二羟基化作用：阿扎庚烷和诺奇霉素类似物的合成

  摘要：

  d-葡萄糖衍生的α，β-不饱和酯3的不对称二羟基化提供了具有良好至高非对映选择性的合成邻二醇。这些邻位二醇通过叠氮化钠转化为相应的环状硫酸盐，区域，立体选择性亲核开环和LAH还原，得到氨基庚糖醇7a，b，其被转化为氮杂环庚烷1c，d和诺奇霉素类似物2c，d。

  DOI：

  10.1021/jo049509t
• 作为产物：
  描述：

  (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 在 sodium tetrahydroborate 、 sodium periodate 、 sodium azide 、 硼酸三甲酯 、 palladium 10% on activated carbon 、 甲酸铵 、 silica gel 、 碳酸氢钠 、 红铝 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 75.66h， 生成 6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose
  参考文献：
  名称：

  Regioselective epoxide opening of epoxyamides derived from d-glucose. Cyclization approaches to azepanes

  摘要：

  Epoxyamides obtained from n-glucose have been evaluated as tools to obtain polyhydroxyazepanes. The stereoselectivity in formation of the epoxyamides was proven to be dependent of the protecting group. The conversion of epoxyamides into epoxyalcohols was necessary to obtain polyhydroxyazepanes, because the direct cyclization of 2-N-amides to azepanecarboxamides was unsuccessful from derivatives obtained from n-glucose. Epoxyamides and epoxyalcohols were regioselectively (alpha) opened by nitrogen nucleophiles. Reduction of diethyl epoxyamide by catalytic transfer hydrogenation gave the alpha deoxy product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.12.005

文献信息

• Synthesis of azepane and nojirimycin iminosugars: the Sharpless asymmetric epoxidation of d-glucose-derived allyl alcohol and highly regioselective epoxide ring opening using sodium azide
  作者：Vrushali H. Jadhav、Omprakash P. Bande、Vedavati G. Puranik、Dilip D. Dhavale

  DOI：10.1016/j.tetasy.2010.01.007

  日期：2010.2

  The Sharp less asymmetric epoxidation of D-glucose-derived ally! alcohol 4 afforded alpha- and beta-epoxides 5a and 5b in high stereoselectivity. The epoxide ring opening in 5a/5b was studied with different nucleophilic azido reagents, under various reaction conditions, and was found to be highly regioselective to give the preferential formation of 6-azido diol 6a/6b over 5-azido-diol 7a/7b. The 6-azido diol 6a/6b and 5-azido dial 7a/7b thus obtained were converted to the corresponding seven- and six-membered iminosugar, namely, azepane 1a/1b and 1-deoxy-nojirimycin 2a/2b. (C) 2010 Elsevier Ltd. All rights reserved.