methyl 2,3,4-tri-O-acetyl-β-L-rhamnopyranoside | 31085-67-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-β-L-rhamnopyranoside
• 英文别名: methyl α-L-rhamnopyranoside triacetate；methyl α-L-rhamnoside triacetate；methyl-(tri-O-acetyl-β-L-rhamnopyranoside)；Methyl-(tri-O-acetyl-β-L-rhamnopyranosid)；[(2S,3S,4R,5R,6S)-4,5-diacetyloxy-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 31085-67-3
• 化学式: C₁₃H₂₀O₈
• 分子量: 304.297
• InChiKey: RTVWBDNQHISFHI-HQXRFNHTSA-N

物化性质

• 熔点：
  151-152 °C
• 沸点：
  341.4±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-β-L-rhamnopyranoside 在 甲醇 、 氨 作用下， 生成 (2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  Fischer et al., Chemische Berichte, 1920, vol. 53, p. 2362,2376, 2382

  摘要：

  DOI：
• 作为产物：
  描述：

  4-O-acetyl-2,3-O-carbonyl-α-L-rhamnopyranosyl bromide 在 吡啶 、 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 20.0h， 生成 methyl 2,3,4-tri-O-acetyl-β-L-rhamnopyranoside
  参考文献：
  名称：

  β-1-鼠李糖吡喃糖苷的合成及13C-nmr光谱

  摘要：

  摘要基于4的使用，合成甲基β-1-鼠李糖吡喃糖苷，6-O-β-鼠李糖吡喃糖基-d-葡萄糖和-d-半乳糖和4-O-β-鼠李糖吡喃糖基-l-鼠李糖。描述了-O-乙酰基-2，3-O-羰基-α-1-鼠李糖基吡喃糖基溴化物作为糖基化剂。将β-1-鼠李糖苷的13 Cn.mr光谱与相应的α端基异构体的光谱进行比较。

  DOI：

  10.1016/s0008-6215(00)85553-6

文献信息

• Radical oxygenation of 2-deoxy-2-iodo hexopyranosides with molecular oxygen
  作者：Stéphane Moutel、Jacques Prandi

  DOI：10.1016/0040-4039(94)88272-x

  日期：1994.10

  2-Deoxy-2-iodo hexopyranosides react with molecular oxygen and tributylstannane to give the epimeric C-2 alcohols in high yield and moderate selectivity.

  2-脱氧-2-碘六吡喃糖苷与分子氧和三丁基锡烷反应，以高收率和适度的选择性产生差向异构的C-2醇。
• Studies on the constituents of Momordica cochinchinensis Spreng. I. Isolation and characterization of the seed saponins, momordica saponins I and II.
  作者：MASAYO IWAMOTO、HIKARU OKABE、TATSUO YAMAUCHI、MASAKO TANAKA、YOSHIE ROKUTANI、SHUJI HARA、KUNIHIDE MIHASHI、RYUICHI HIGUCHI

  DOI：10.1248/cpb.33.464

  日期：——

  The structures of momordica saponins I and II, the seed saponins of Momordica cochinchinensis SPRENG. (Cucurbitaceae) have been elucidated on the basis of spectral and chemical evidence as the 3-O-β-D-galactopyranosyl (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-glucuronopyranosido-28-O-β-D-xylopyranosyl (1→3)-β-D-glucopyranosyl (1→3)-[β-D-xylopyranosyl (1→4)]-α-L-rhamnopyranosyl (1→2)-β-D-fucopyranosides of gypsogenin and quillaic acid, respectively. I and II are contained in the seed kernels in a carboxylate form.

  根据光谱和化学证据，阐明了葫芦科植物 Momordica cochinchinensis SPRENG.(根据光谱和化学证据，阐明了葫芦科植物 Momordica cochinchensis SPRENG 的种子皂苷 I 和 II 的结构为 3-O-β-D-吡喃半乳糖基 (1→2)-[α-L-rhamnopyranosyl (1→3)]-β-D-Glucuronopyranosido-28-O-β-D-吡喃木糖(1→3)-β-D-吡喃葡萄糖基(1→3)-[β-D-吡喃木糖(1→4)]-α-L-吡喃鼠李糖基(1→2)-β-D-吡喃岩藻糖苷的石膏苷元和紫苏酸、分别为 I 和 II。I 和 II 以羧酸形式存在于种仁中。
• Direct Glycosylation of Unprotected and Unactivated Sugars Using Bismuth Nitrate Pentahydrate
  作者：Innaiah K. Polanki、Siva H. Kurma、Asish K. Bhattacharya

  DOI：10.1080/07328303.2015.1028585

  日期：2015.5.4

  Bi(NO3)(3), a low-cost, mild, and environmentally green catalyst, has been successfully utilized for Fischer glycosylation for the synthesis of alkyl/aryl glycopyranosides by reacting unprotected sugars, namely, D-glucose, L-rhamnose, D-galactose, D-arabinose, and N-acetyl-D-glucosamine with various alcohols in good to excellent yields. The glycosides were formed with high alpha-selectivity. Further, an expedient separation of alpha- and beta-glycosides using silver nitrate-impregnated silica gel flash liquid chromatography has been developed.
• 2-METHYL-l-RHAMNOSE AND 2-METHYL-d-FUCOSE AND THEIR BEARING ON THE CONFIGURATION OF DIGITALOSE
  作者：HAROLD B. MacPHILLAMY、ROBERT C. ELDERFIELD

  DOI：10.1021/jo01214a009

  日期：1939.5
• The Reaction of Tribenzoyl-α-L-rhamnopyranosyl Bromide with Methanol. Various Benzoylated Derivatives of L-Rhamnose
  作者：Robert K. Ness、Hewitt G. Fletcher、C. S. Hudson

  DOI：10.1021/ja01145a097

  日期：1951.1