methyl 2,6-dideoxy-β-D-ribo-hexopyranoside | 4092-45-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-dideoxy-β-D-ribo-hexopyranoside
• 英文别名: Methyl-β-D-digitoxopyranoside；(+)-methyl α-D-digitoxoside；methyl β-D-digitose；Methyl-β-D-digitoxopyranosid；(2R,3S,4S,6R)-6-methoxy-2-methyloxane-3,4-diol
• CAS: 4092-45-9；13322-79-7；17676-16-3；17676-19-6；19131-10-3；19131-11-4；33985-35-2；40878-56-6；53293-94-0；56733-47-2；62346-15-0；71305-70-9；72204-04-7；77210-24-3；78853-88-0；92007-64-2；133814-52-5；139756-72-2
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: QNKOVWCOVLYPKR-XZBKPIIZSA-N

物化性质

• 沸点：
  273.7±40.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,6-dideoxy-β-D-ribo-hexopyranoside 在 吡啶 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside 在 吡啶 、 四丁基亚硝酸铵 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 15.5h， 生成 methyl 2,6-dideoxy-β-D-ribo-hexopyranoside
  参考文献：
  名称：

  Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124

  摘要：

  DOI：

文献信息

• The Asymmetric Syntheses of Methyl <small>D</small>-Digitoxoside, <small>L</small>-Oleandrose and <small>L</small>-Cymarose from Methyl Sorbate, an Achiral Precursor
  作者：Machiko Ono、Xi Ying Zhao、Keisuke Kato、Hiroyuki Akita

  DOI：10.1248/cpb.c12-00308

  日期：——

  addition product (+)-(3S,4S,5R)-9 possessing a 3,4-cis-dihydroxy-δ-lactone in 78% overall yield from (4S,5R)-4. The obtained (+)-(3S,4S,5R)-9 was subsequently converted to methyl D-digitoxoside (pyranoside) (12) in 13% overall yield and methyl D-digitoxoside (furanoside) (12) in 20% overall yield. The reaction of benzyl-osmundalactone (4R,5S)-3 and MeOH in the presence of Amberlyst A-26 as a basic catalyst

  向渗透性内酯（4S，5R）-4中添加4 eq的氯醛可定量形成半缩醛衍生物（4S，5R）-8，将其用甲烷磺酸处理，得到分子内的Micheal加成产物（+）-（具有3,4-顺式-二羟基-δ-内酯的3S，4S，5R）-9从（4S，5R）-4的总产率为78％。随后将获得的（+）-（3S，4S，5R）-9转化为总产率为13％的甲基D-数字氧苷（吡喃糖苷）（12）和总产率为20％的甲基D-数字氧苷（呋喃糖苷）（12） 。在Amberlyst A-26作为碱性催化剂的存在下，苄基-磺基内酯（4R，5S）-3与MeOH的反应得到3,4-trans-δ-内酯（-）-（3S，4R，5S）-20产率为28％，3,4-顺-δ-内酯（-）-（3R，4R，5S）-21产率为45％。（-）-（3S，4R，5S）-20的Dibal-H还原反应，然后进行催化加氢得到L-夹竹桃糖（6），总产率为86％，
• Studies on the constituents of Asclepiadaceae plants. LXII. The structures of two glycosides, cynafoside-A and -B, with a novel sugar chain containing a pair of optically isomeric sugars, D- and L-cymaroses, from Cynanchum africanum R. Br.
  作者：SACHIKO TSUKAMOTO、KOJI HAYASHI、HIROSHI MITSUHASHI、FRIEDRICH OTTO SNYCKERS、THEUNIS GERHARDUS FOURIE

  DOI：10.1248/cpb.33.4807

  日期：——

  Two glycosides named cynafoside-A (1) and -B (2) were isolated from Cynanchum africanum R. BR. (Asclepiadaceae) which is toxic to stock in South Africa. Their structures were determined on the basis of spectral and chemical evidence, and are unusual in that they include both D-and L-cymaroses in the sugar chain.

  从对南非的牲畜有毒的 Cynanchum africanum R. BR.（Asclepiadaceae）中分离出两种苷，分别命名为 cynafoside-A（1）和-B（2）。它们的结构是根据光谱和化学证据确定的，其不寻常之处在于糖链中同时包含 D 和 L-香豆素。
• Studies on the constituents of asclepiadaceae plant—LVII
  作者：Sachiko Tsukamoto、Koji Hayashi、Hiroshi Mitsuhashi

  DOI：10.1016/s0040-4020(01)96411-7

  日期：1985.1

  Six new glycosides named wilfoside C3N (l), C1N (2), C2N (3), C3G (4), C1G (5) and C2G (6) were isolated from Cynanchum wilfordi hemsley (Asclepiadaceae) and their structures were deduced on the basis of the chemical and spectral evidence. It is quite unusual that 2, 3, 5 and 6 include both D-cymarose and L-cymarose in each sugar chain.

  六个命名wilfoside C3N（新甙升），C1N（2），C2N（3），C3G（4），C1G（5）和C2G（6）从分离牛心wilfordi昂斯莱（萝藦科）和它们的结构进行了推导出的化学和光谱证据的基础。这是相当不寻常的是2，3，5和6包括在每个糖链既d-cymarose和L-cymarose。
• Intramolecular reactions of carbohydrate triflates
  作者：Roger W. Binkley

  DOI：10.1021/jo00034a030

  日期：1992.4

  Each of the four possible methyl 2,6-dideoxy-beta-D-hexopyranosides (3-6) was treated with an equivalent amount of triflic anhydride in the presence of 2,6-di-tert-butyl-4-methylpyridine (7). The ribo isomer 3 produced both the 3-O-triflyl (8, 15%) and the 4-O-triflyl (9, 73%) derivatives while the lyxo isomer 4 gave only the 3-O-triflyl compound (11, 84%). Upon heating, the triflate 8 lost the elements of triflic acid to form methyl 2,3,6-trideoxy-beta-D-glycero-hexopyranosid-4-ulose (23, 72%), while 9 experienced ring contraction involving the pyranoid ring oxygen to form methyl 3,5-anhydro-2,6-dideoxy-beta-D-xylo-hexofuranoside (20, 54%). Compound 11 produced methyl 3-C-aldehydo-2,5-dideoxy-beta-D-threo-pentofuranoside (13, 65%). Upon reaction with triflic anhydride, methyl 2,6-dideoxy-beta-D-arabino- and -xylo-hexopyranosides (5 and 6, respectively) generated hydroxy triflates which were not isolated due to their further reaction below room temperature. Compound 5 produced aldehyde 13 (54%) while reaction of 6 gave methyl 3,4-anhydro-2,6-dideoxy-beta-D-lyxo- and -ribo-hexopyranosides [15 (48%) and 16 (24%), respectively]. The mechanisms for these reactions are discussed and the reactivity of the hydroxy triflates is compared to that of related carbohydrate derivatives.
• Binkley, Roger W., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 1, p. 111 - 124
  作者：Binkley, Roger W.

  DOI：——

  日期：——