甲基 2,3,4-三-O-乙酰基-6-O-三苯代甲基-β-D-吡喃半乳糖苷 | 87591-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 甲基 2,3,4-三-O-乙酰基-6-O-三苯代甲基-β-D-吡喃半乳糖苷
• 中文别名: 甲基2,3,4-三-O-乙酰基-6-O-三苯代甲基-β-D-吡喃半乳糖苷
• 英文名称: Methyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranoside
• 英文别名: Methyl-2,3,4-tri-O-acetyl-6-O-trityl-β-D-galactopyranosid；methyl-(O²,O³,O⁴-triacetyl-O⁶-trityl-β-D-galactopyranoside)；Methyl-(O²,O³,O⁴-triacetyl-O⁶-trityl-β-D-galactopyranosid)；Methyl-2,3,4-tri-O-acetyl-6-O-triphenylmethyl-β-D-galactopyranosid；METHYL 2,3,4-TRI-O-ACETYL-6-O-TRIPHENYLMETHYL-beta-D-GALACTOPYRANOSIDE；[(2R,3S,4S,5R,6R)-4,5-diacetyloxy-6-methoxy-2-(trityloxymethyl)oxan-3-yl] acetate
• CAS: 87591-35-3
• 化学式: C₃₂H₃₄O₉
• 分子量: 562.617
• InChiKey: CEIHIENXWVDRTC-GGEKVXJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  41
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基 2,3,4-三-O-乙酰基-6-O-三苯代甲基-β-D-吡喃半乳糖苷 生成 methyl (methyl 2,3,4-tri-O-acetyl-β-D-galactopyranosid)uronate
  参考文献：
  名称：

  BETANELI, VITALI I.;OTT, ANDREJ YA.;BRUKHANOVA, OLGA V.;KOCHETKOV, NIKOLA+, CARBOHYDR. RES., 179,(1988) C. 37-50

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基-Β-D-吡喃半乳糖苷 在 吡啶 作用下， 反应 27.0h， 生成 甲基 2,3,4-三-O-乙酰基-6-O-三苯代甲基-β-D-吡喃半乳糖苷
  参考文献：
  名称：

  A Facile, One‐Step Conversion of 6‐O‐Trityl and 6‐O‐TBDMS Monosaccharides into the Corresponding Formate Esters

  摘要：

  A convenient method has been developed for a facile and high-yield conversion of 6-O-tertbutyldimethylsilyl and 6-O-trityl protected monosaccharides to their formate esters, which may serve as useful intermediates for the replacement of the primary hydroxyl group of sugars by other functional groups.

  DOI：

  10.1080/07328300600859668

文献信息

• A Mild, Highly Efficient, and Chemoselective Deprotection of Trityl Ethers of Carbohydrates and Nucleosides Using Iodine Monobromide¹
  作者：K. P. Kartha、Satish Malik

  DOI：10.1055/s-0029-1217356

  日期：2009.7

  Iodine monobromide in dichloromethane-methanol or acetonitrile constitutes an effective reagent for the deprotection of O-trityl and O-dimethoxytrityl ethers of carbohydrates and nucleosides. Acid-labile functionalities (acetals, O-p-methoxybenzyl ethers, etc.) as well as base-labile groups (esters and amides) are stable under these conditions; and the method has been found to be superior to the hitherto known literature methods.

  在二氯甲烷-甲醇或乙腈中，一溴化碘构成了一种有效的试剂，用于去保护碳水化合物和核苷的O-三苯甲基和O-二甲氧基三苯甲基醚。酸性敏感功能团（如缩醛、O-对甲氧基苄基醚等）以及碱性敏感基团（如酯和酰胺）在这些条件下是稳定的；并且该方法已被发现优于迄今已知的文献方法。
• Formation of 6-deoxy-6-iodohexopyranosides as substrates for the hex-5-enose degradation
  作者：Gerald O. Aspinall、Roshan C. Carpenter、Lev Khondo

  DOI：10.1016/0008-6215(87)80105-2

  日期：1987.8

  and poly-saccharide derivatives. It is shown that ( 1 ) unsubstituted d -glucopyranosides undergo selective, primary iodination without unwanted side-reactions; ( 2 ) primary iodination of d -galactopyranosides is accompanied by 3,6-anhydride formation, so that the desired reaction is only possible with protection of secondary hydroxyl groups; and ( 3 ) the extent of iodination in substrates of higher

  摘要研究了一系列单，双和多糖衍生物的6-脱氧-6-碘己吡喃果糖苷作为六-戊糖降解的潜在底物的合成方法。结果表明：（1）未取代的d-吡喃葡萄糖苷经过选择性的初级碘化反应而没有不希望的副反应。（2）d-吡喃半乳糖苷的初级碘化反应伴随着3，6-酐的形成，因此所需的反应只有在保护仲羟基的情况下才有可能。（3）通过使乙酰化的（或甲基化的）衍生物与三丁基锡烷反应，然后分析所得的6-脱氧己吡喃糖苷，方便地确定较高分子量的底物中的碘化程度。
• Synthesis of 1,2-O-cyanoethylidene derivatives of alkyl glycopyranuronates by oxidation of the 6-trityl ethers of their hexose analogues
  作者：Vitali I. Betaneli、Andrej Ya. Ott、Olga V. Brukhanova、Nikolay K. Kochetkov

  DOI：10.1016/0008-6215(88)84108-9

  日期：1988.8

  derivatives (CED) of alkyl glycopyranuronates with the d -Glc, d -Gal, and d -Man configurations is described by oxidation of the 3,4-di-O-acetyl-6-O-trityl-CED-hexose analogues with the Jones reagent [chromium(VI) oxide-sulfuric acid]. The isopropylidenation of hydroxyl-containing triphenylmethyl ethers is demonstrated.

  摘要通过氧化3,4-二-O-乙酰基-6，描述了具有d -Glc，d -Gal和d -Man构型的吡喃葡萄糖醛酸烷基酯的1,2-O-氰基亚乙基衍生物（CED）的合成。 -O-三苯甲基-CED-己糖类似物与琼斯试剂[氧化铬（VI）-硫酸]。证明了含羟基的三苯基甲基醚的异丙基化。
• Synthesis and characterization of methyl 6-O-α- and -β-d-galactopyranosyl-β-d-galactopyranoside
  作者：Pavol Kováč、Edward A. Sokoloski、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(84)85088-0

  日期：1984.5

  disaccharides (7 and 9, respectively) in high yield, and their structure was confirmed by 1H- and 13C-n.m.r. 1d. and 2d. spectroscopy. O-Deacetylation of 7 gave the hitherto unknown, crystalline methyl 6-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside. O-Deacetylation of 9 gave the corresponding, beta-D-linked disaccharide methyl glycoside, the physical constants of which are discussed with respect to controversial

  依次对甲基β-D-吡喃半乳糖苷进行三苯甲基化，乙酰化和去三苯甲基化，得到结晶的甲基2,3,4-三-O-乙酰基-β-D-吡喃半乳糖苷（4）和甲基2,3,6-三-O-乙酰基-甲基β-D-吡喃半乳糖苷，后者是乙酰迁移引起的次要产物。在氰化汞和溴化汞的存在下，4与2,3,4,6-四-O-乙酰基-α-D-半乳糖基溴在苯中的反应得到α-和β-D-（1-- --6）-连接的二糖（分别为7和9），产率很高，其结构由1H-和13C-nmr 1d证实。和2d。光谱学。7的O-脱乙酰化产生了迄今未知的结晶甲基6-O-α-D-吡喃半乳糖基-β-D-吡喃半乳糖苷。9的O-脱乙酰基化得到相应的β-D连接的二糖甲基糖苷，
• 2-Methyl- and 2,6-Dimethylgalactose
  作者：John Walter Hyde Oldham、David James Bell

  DOI：10.1021/ja01269a026

  日期：1938.2

表征谱图