methyl β-D-digitoxofuranoside | 58066-71-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl β-D-digitoxofuranoside
• 英文别名: (2R,3S,5R)-2-[(1R)-1-hydroxyethyl]-5-methoxyoxolan-3-ol
• CAS: 58066-71-0；78798-12-6；78798-13-7；88756-99-4；130169-81-2；130169-82-3；130169-87-8；130169-89-0；130169-90-3；143087-71-2；58066-72-1
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: SOMLFJGHYAZCRX-XZBKPIIZSA-N

物化性质

• 沸点：
  295.4±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)：
  -0.51
• 重原子数：
  11.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  dimethyl acetal of 2,6-dideoxy-D,L-ribohexose 生成 methyl β-D-digitoxofuranoside
  参考文献：
  名称：

  ARSHAVA, B. M.;RAJFELD, YU. E.;MAKIN, S. M., ZH. ORGAN. XIMII, 26,(1990) N, S. 778-785

  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％，
• Ammocidin, a New Apoptosis Inducer in Ras-dependent Cells from Saccharothrix sp. II. Physico-chemical Properties and Structure Elucidation.
  作者：RYO MURAKAMI、TAIJIRO TOMIKAWA、KAZUO SHIN-YA、JUNKO SHINOZAKI、TAKAYUKI KAJIURA、HARUO SETO、YOICHI HAYAKAWA

  DOI：10.7164/antibiotics.54.714

  日期：——

  The structure of ammocidin, a new apoptosis inducer in Ras-dependent cells from Saccharothnx sp. AJ9571, was elucidated to be as shown in Fig. 1 by NMR and degradation studies. Ammocidin consists of a 20-membered macrolide ring and three deoxy sugars identified as 6-deoxy-L-glucose, D-digitoxose and D-olivomycose.

  ammocidin 的结构，一种来自 Saccharothnx sp 的 Ras 依赖性细胞的新型凋亡诱导剂。通过NMR和降解研究表明AJ9571如图1所示。阿莫西丁由 20 元大环内酯环和三种脱氧糖组成，分别为 6-脱氧-L-葡萄糖、D-洋地黄糖和 D-橄榄菌糖。
• Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate
  作者：Robert M. Giuliano、Frank J. Jr. Villani

  DOI：10.1021/jo00106a035

  日期：1995.1

  The additions of organometallic reagents to two pentodialdo-1,4-furanosides (methyl 3-O-benzyl-2-deoxy-alpha-D-erythro-pentofuranoside and its beta-anomer) were carried out under a variety of experimental conditions. Methylmagnesium halides, methyllithium, methylcerium and the organotitanium reagent MeTi(OiPr)(3) were reacted with the pentodialdo-1,4-furanosides in an effort to determine if the stereoselectivity of addition to the formyl group is the result of chelation or nonchelation control and to determine the effect of anomeric configuration. The stereochemistry of the products was assigned by NMR methods and correlation with known compounds synthesized previously. The stereoselectivity of addition depends on the configuration at the anomeric center of the dialdose, with the beta-anomer giving mainly the product of a non-chelation-controlled addition and the beta-anomer giving the opposite stereoselectivity. The major product obtained from the beta-anomer was utilized as a key intermediate in the synthesis of two branched-chain carbohydrates, axenose and evermicose, found in antibiotics. Methylcerium additions are the most efficient method for introducing the branching methyl group in a 2-deoxyfuranosid-3-ulose.
• Arshava, B. M.; Raifel'd, Yu. E.; Makin, S. M., Journal of Organic Chemistry USSR (English Translation), 1990, vol. 26, # 4, p. 666 - 672
  作者：Arshava, B. M.、Raifel'd, Yu. E.、Makin, S. M.

  DOI：——

  日期：——