(2S,3R,4S,5S,6R)-2,3,4,5-Tetramethoxy-6-methoxymethyl-tetrahydro-pyran | 3149-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5S,6R)-2,3,4,5-Tetramethoxy-6-methoxymethyl-tetrahydro-pyran
• 英文别名: methyl 2,3,4,6-tetra-O-methyl-α-D-galactopyranoside；methyl 2,3,4,6-tetra-O-methyl-α-D-galactopyranose；permethylated α-D-(+)-galactopyranoside；methyl-(tetra-O-methyl-α-D-galactopyranoside)；Methyl-(tetra-O-methyl-α-D-galactopyranosid)；alpha-D-Galactopyranoside, methyl 2,3,4,6-tetra-O-methyl-；(2S,3R,4S,5S,6R)-2,3,4,5-tetramethoxy-6-(methoxymethyl)oxane
• CAS: 3149-64-2
• 化学式: C₁₁H₂₂O₆
• 分子量: 250.292
• InChiKey: ZYGZAHUNAGVTEC-KJPMQGKISA-N

物化性质

• 保留指数：
  1468

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S,6R)-2,3,4,5-Tetramethoxy-6-methoxymethyl-tetrahydro-pyran 在 氢溴酸 、 溴 作用下， 生成 O²,O³,O⁴,O⁶-tetramethyl-D-galactonic acid-lactone
  参考文献：
  名称：

  Humphreys; Pryde; Waters, Journal of the Chemical Society, 1931, p. 1299

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3R,4R,5R,6R)-2-[(2S,3R,4S,5S,6R)-2-[[(2S,4aR,4bR,6aS,7R,8R,10aR,10bR,12aR)-7-hydroxy-8-(hydroxymethyl)-8-[(E)-5-hydroxy-4-methylpent-3-enyl]-1,1,4a,10a,10b-pentamethyl-3,4,4b,5,6,6a,7,9,10,11,12,12a-dodecahydro-2H-chrysen-2-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol 生成 (2S,3R,4S,5S,6R)-2,3,4,5-Tetramethoxy-6-methoxymethyl-tetrahydro-pyran
  参考文献：
  名称：

  FUJIOKA, TOSHIHIRO;IWAMOTO, MASAYO;IWASE, YUKIKO;OKABE, HIKARU;MIHASHI, K+, CHEM. AND PHARM. BULL., 36,(1988) N 8, C. 2772-2777

  摘要：

  DOI：

文献信息

• Methylation of methyl α-d-hexopyranosides with diazo-methane in the presence of a small amount of water
  作者：Yuko Inoue、Kinzo Nagasawa

  DOI：10.1016/0008-6215(87)80024-1

  日期：1987.11

  Abstract The long-time reduction of methyl α- d -gluco-, α- d -manno-, and α- d -galactopyranosides with excess diazomethane-diethyl ether at 25° in the presence of water gave all partially methylated methyl α- d -hexopyranosides which differ in number and position of methyl substitution. The presence of electrolytes, such as potassium or sodium phosphate, in the reaction medium enhanced the degree of methylation

  摘要在水存在下，用过量的重氮甲烷-二乙醚在25°下长时间还原甲基α-d-葡萄糖-，α-d-甘露糖和α-d-吡喃半乳糖苷，所有部分甲基化的甲基α-d -甲基吡喃糖苷的数目和位置不同。反应介质中电解质（例如磷酸钾或磷酸钠）的存在增强了甲基化的程度，从而导致优先形成甲基α-d-己基吡喃糖苷的三-O-甲基衍生物。
• Fluorine-Directed β-Galactosylation: Chemical Glycosylation Development by Molecular Editing
  作者：Estelle Durantie、Christoph Bucher、Ryan Gilmour

  DOI：10.1002/chem.201200468

  日期：2012.6.25

  Validation of the 2‐fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2‐fluoro‐3,4,6‐tri‐O‐benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization

  提出了将2-氟取代基作为控制化学糖基化反应的惰性指导基团的验证方法。一项分子编辑研究表明，通过使用2-氟-3,4,6-三-O-苄基吡喃葡萄糖基三氯乙酰亚氨酸酯（TCA）支架，糖基化过程中非对映异构控制的异常水平是2 R，3 S，4的结果S立体三合会。这项研究还表明，C4的差向异构作用会导致β选择性大大提高（高达β/α300：1）。
• Study on the constituents of Desmodium styracifolium.
  作者：Tomoko KUBO、Syuichi HAMADA、Toshihiro NOHARA、Zhi-rou WANG、Hideo HIRAYAMA、Keiichi IKEGAMI、Ken YASUKAWA、Michio TAKIDO

  DOI：10.1248/cpb.37.2229

  日期：——

  Two triterpenoid saponins (1 and 2) were isolated from Desmodii Herba [the dried whole plants of Desmodium styracifolium (Osbeck) Merr. (Leguminosae)] and their chemical structures were characterized as soyasaponin I and a new saponin, 3-O-[alpha-L-rhamnopyranosyl-(1----2)-beta-D-galactopyranosyl- (1----2)-beta-D-glucuronopyranosyl]soyasapogenol E, respectively, by chemical and spectroscopic means

  从Desmodii Herba [满地香（Desmodium styracifolium（Osbeck）Merr）干燥的整株植物中分离出了两个三萜皂苷（1和2）。（豆科）]及其化学结构被表征为大豆皂苷I和新的皂苷3-O- [α-L-鼠李糖基-（1 ---- 2）-β-D-吡喃半乳糖基-（1 ---- 2）通过化学和光谱方法分别测定β-D-D-葡萄糖醛酸吡喃糖基]大豆皂酚E。
• 1 : 1 Adduct Ion Formation of Permethylated Monosaccharides with Organic Cations in FAB Mass Spectrometry
  作者：Masami Sawada、Li Ouyang、Yoshio Takai、Hitoshi Yamada、Motohiro Shizuma、Takeshi Kinoshita、Tomoko Mochizuki、Terukiyo Hanafusa

  DOI：10.1246/bcsj.64.1243

  日期：1991.4

  the OCH3 configurational effects of M on (M+A)+ adduct ion formation. The findings can be interpreted in terms of multisite electrostatic interaction of oxygens with the cation. Coupled with the results of gas-phase behavior by FABMS/MS(CAD), solution behavior by 1H NMR, and model calculations by MNDO, the characteristic structure of the 1 : 1 adduct ion is deduced as host-guest type association between

  已在定量 FAB 质谱法中检查了一系列全甲基化单糖 (M; Ia–Ih) 和有机或金属阳离子 (A+) 之间 1:1 的加合离子形成。在相同 FABMS 条件下的仔细比较中，相对 (M+A)+ 峰强度以单糖的以下顺序增加，并进一步以几乎相同的程度增加，尽管使用了三种不同的阳离子，例如辛基铵，（甲氧基羰基） ) 甲基铵和钾离子：β-Glc<α-Glc<α-Gal<β-Gal≤α-Man<β-Man<α-Tal<β-Tal。顺序和阳离子独立性清楚地表明 OCH3 构型M 对 (M+A)+ 加合离子形成的影响。这些发现可以解释为氧与阳离子的多位点静电相互作用。
• Mechanism of anomerization of permethylated methyl d-glycopyranosides by trimethylsilyl trifluoromethanesulfonate
  作者：Chang Kiu Lee、Eun Ju Kim、In-Sook Han Lee

  DOI：10.1016/s0008-6215(98)00132-3

  日期：1998.7

  Abstract Anomerization of permethylated methyl d -glycopyranosides catalyzed by trimethylsilyl trifluoromethanesulfonate was examined by NMR spectroscopy and gas–liquid chromatography. The initial-rate analysis showed that the rates of anomerization of β to α were faster than those of the opposite at various concentrations of the catalyst. The overall rates of disappearance of the substrates were faster

  摘要用三氟甲磺酸三甲基甲硅烷基酯（NMR）和气相色谱法研究了全甲基化的甲基d-吡喃葡萄糖苷的三元甲硅烷基化反应。初始速率分析表明，在不同的催化剂浓度下，β到α的异化速率要快于相反的速率。底物的总消失速率比相反的端基异构体的出现速率快，这是因为形成了yl型化合物。后者的结构是基于1 H和13 C NMR光谱提出的，尽管它是不可分离的。环状和无环的氧鎓离子似乎都是异构化的中间体。前者似乎是形成吡啶型化合物以及α-糖苷键的异构化的关键中间体。