methyl 3,4-anhydro-6-deoxy-β-L-arabino-hex-5-enopyranoside | 58635-67-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4-anhydro-6-deoxy-β-L-arabino-hex-5-enopyranoside
• 英文别名: (1R,4S,5R,6R)-4-methoxy-2-methylidene-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 58635-67-9
• 化学式: C₇H₁₀O₄
• 分子量: 158.154
• InChiKey: FPWNCKXHMVNBMC-UCROKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,4-anhydro-6-deoxy-β-L-arabino-hex-5-enopyranoside 在 sodium methylate 作用下， 以 丙酮 为溶剂， 反应 0.67h， 生成 Methyl 4-S-(3-azido-4-α-maltotriosyloxybutyl)-6-deoxy-4-thio-α-D-xylo-hex-5-enopyranoside
  参考文献：
  名称：

  Photolabile, spacer-modified oligosaccharides for probing malto-oligosaccharide binding sites in proteins

  摘要：

  O-Deacylation and S-deacylation of the diastereomers of 2-azido-4-S-benzoyl-4-mercaptobutyl 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranoside (9) with methanolic sodium methoxide and coupling of the resulting thiol to methyl 3,4-anhydro-6-deoxy-beta-L-arabino-hex-5-enopyranoside (2) gave the corresponding diastereomers of the spacer-modified disaccharide methyl 4-S-(3-azido-4-alpha-D-glucopyranosyloxybutyl)-6-deoxy-4-thio-alph a-D-xylo-hex-5-enopyranoside (10). Glucosylation of the diastereomers of 10 with alpha-cyclo-dextrin-CGTase and treatment of the products with beta-amylase gave the diastereomers of the spacer-modified oligosaccharides methyl 4-S-(3-azido-4-alpha-maltosyloxybutyl)-6-deoxy-4-thio-alpha-D-xylo -hex-5-enopyranosides (11) and 4-S-(3-azido-4-alpha-maltotriosyloxybutyl)-6-deoxy-4-thio-alpha-D- hex-5-enopyranosides (12). The diastereomers of 10 each had a good affinity for pancreatic alpha-amylase and the maltose-binding protein from E. coli. The affinities of the diastereomers of 11 and 12 were higher by at least one order of magnitude.

  DOI：

  10.1016/0008-6215(90)80131-l
• 作为产物：
  描述：

  methyl 2,3-di-O-acetyl-6-deoxy-4-O-(4-toluenesulfonyl)-α-D-xylo-hex-5-enopyranoside 在 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 methyl 3,4-anhydro-6-deoxy-β-L-arabino-hex-5-enopyranoside
  参考文献：
  名称：

  三种区域异构的光不稳定配体对猪-胰腺α-淀粉酶中底物结合区的差异化学修饰

  摘要：

  三种区域异构的放射性标记的间隔基修饰的寡糖：甲基4'-O- [4-S-（3-azi-4-alpha-D-吡喃葡萄糖基氧基-1- [3H]丁基）-6-脱氧-4-硫代-α- D-xylo-hex-5-enopyranosyl] -alpha-maltoside（12a，G1-G3 *），甲基4-O- [4-S-（3-azi-4-alpha-maltosyloxy-1- [3H] butyl] ）-6-脱氧-4-t硫代-α-D-木酮-己糖-5-烯吡喃糖基]-α-D-吡喃葡萄糖苷（15a，G2-G2 *）和甲基4-S-（3-azi-4-合成了α-麦芽三糖基氧基-1- [3H]丁基）-6-脱氧-4-th-α-D-xylo-hex-5-enopyranoside（16a，G3-G1 *）并用作该化学试剂的光亲和探针猪胰α-淀粉酶（PPA）的修饰。共价结合的放射性的掺入达到化学计量值的25-38％。三种标记蛋白制剂PPA-G1-G3

  DOI：

  10.1016/0008-6215(94)00225-8

文献信息

• Spacer-modified, photolabile tetrasaccharides as analogues of maltopentaose are versatile probes for porcine pancreatic alpha-amylase
  作者：Jochen Lehmann、Lothar Ziser

  DOI：10.1016/0008-6215(92)80041-x

  日期：1992.2

  The syntheses are described of methyl 4'-O-[4-S-(3-azi-4-alpha-D-glucopyranosyloxybutyl)-6-deoxy-4 -thio-alpha-D-xylo-hex-5-enopyranosyl]-alpha-maltoside (28), methyl 4-O-[4-S-(3-azi-4-alpha-maltosyloxybutyl)-6-deoxy-4-thio- alpha-D-xylo-hex-5-enopyranosyl]-alpha-D-glucopyranoside (29), and methyl 4-S-(3-azi-4-alpha-maltotriosyloxybutyl)-6-deoxy-4-thio- alpha-D-xylo-hex-5-enopyranoside (30), which

  描述了甲基4'-O- [4-S-（3-azi-4-α-D-吡喃葡萄糖基氧基丁基）-6-脱氧-4-硫代-α-D-二甲苯基-己基-5-enopyranosyl]的合成。 -α-麦芽糖苷（28），甲基4-O- [4-S-（3-azi-4-α-麦芽糖基氧基丁基）-6-脱氧-4-硫代-α-D-木糖己基-5-烯吡喃糖基] -α-D-吡喃葡萄糖苷（29）和甲基4-S-（3-azi-4-α-麦芽三糖基氧基丁基）-6-脱氧-4-硫代-α-D-二甲苯基-六-5-烯吡喃糖苷（30） ，是麦芽五糖的类似物，其中一个中央葡糖基单元被带有光不稳定azi基的无环四元烃间隔基取代。高浓度的胰腺α-淀粉酶仅缓慢裂解30个。Ki值（mM）为0.15（28），2.1（29）和2.5（30）。在严重存在28-30的条件下，通过辐射使酶失活分别为96.4％，98.1％和40％。
• LEHMANN, JOCHEN;ZISER, LOTHAR, CARBOHYDR. RES., 205,(1990) C. 93-103
  作者：LEHMANN, JOCHEN、ZISER, LOTHAR

  DOI：——

  日期：——