(3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester | 131591-67-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester
• 英文别名: 3-O-carbomethoxymethyl-1,2:5,6-di-O-isopropylodene-α-D-glucofuranose；3-O-carboxymethyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose；O¹,O²;O⁵,O⁶-diisopropylidene-O³-methoxycarbonylmethyl-α-D-glucofuranose；O¹,O²;O⁵,O⁶-Diisopropyliden-O³-methoxycarbonylmethyl-α-D-glucofuranose；methyl 2-[[(3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl]oxy]acetate
• CAS: 131591-67-8
• 化学式: C₁₅H₂₄O₈
• 分子量: 332.351
• InChiKey: DXPNPGDIVDLRPN-KABOQKQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 O³-(2-hydroxy-ethyl)-D-glucose
  参考文献：
  名称：

  SYNTHESIS OF FOUR CARBOXYMETHYL ETHERS OF GLUCOSE

  摘要：

  2-, 3- 和 6-O-羧甲基-D-葡萄糖以及2,3-二-O-羧甲基-D-葡萄糖已经被合成。找到了一种溶剂系统，可以完全地在纸层析中分离这些衍生物，以及从羧甲基纤维素水解得到的衍生物。

  DOI：

  10.1139/v56-080
• 作为产物：
  描述：

  双丙酮葡萄糖 在 乙醚 、 sodium 作用下， 生成 (3aR,4R,5R,6S,6aR) [5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-yloxy]acetic acid methyl ester
  参考文献：
  名称：

  SYNTHESIS OF FOUR CARBOXYMETHYL ETHERS OF GLUCOSE

  摘要：

  2-, 3- 和 6-O-羧甲基-D-葡萄糖以及2,3-二-O-羧甲基-D-葡萄糖已经被合成。找到了一种溶剂系统，可以完全地在纸层析中分离这些衍生物，以及从羧甲基纤维素水解得到的衍生物。

  DOI：

  10.1139/v56-080

文献信息

• Synthesis of Oxepane Ring Containing Monocyclic, Conformationally Restricted Bicyclic and Spirocyclic Nucleosides from <scp>d</scp>-Glucose:  A Cycloaddition Approach
  作者：Subhankar Tripathi、Biswajit G. Roy、Michael G. B. Drew、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1021/jo070846m

  日期：2007.9.1

  C-3-O-allyl, (ii) C-4 vinyl and a C-3-O-tethered nitrone, and (iii) C-5 nitrone and C-4-allyloxymethyl generated tetracyclic isoxazolidinooxepane/-pyran ring systems upon intramolecular nitrone cycloaddition reactions. Deprotection of the 1,2-acetonides of these derivatives followed by introduction of uracil base via Vorbrüggen reaction condition and cleavage of the isooxazolidine rings as well as of benzyl

  具有（i）C-5硝酮和C-3- O-烯丙基，（ii）C-4乙烯基和C-3- O的碳水化合物衍生的底物分子内的硝酮环加成反应生成的四环异恶唑烷氧杂环庚烷/吡喃环系统生成了束缚的硝酮，以及（iii）C-5硝酮和C-4-烯丙氧基甲基。将这些衍生物的1,2-丙酮化物脱保护，然后通过Vorbrüggen反应条件引入尿嘧啶碱基，并通过转移氢解作用裂解异恶唑烷环以及苄基，得到含有双环和螺环核苷的氧杂环丁烷环。通过切割异恶唑烷和呋喃糖环，将产生的氨基官能团与5-氨基-4,6-二氯嘧啶偶联，环化为嘌呤环，最后进行氨解，制备相应的基于氧杂环丁烷的核苷类似物。
• Thiourea:  A Novel Cleaving Agent for 1,3-Dioxolanes
  作者：Swapan Majumdar、Anup Bhattacharjya

  DOI：10.1021/jo981115c

  日期：1999.7.1
• 4-Acetamidophenyl esters and 4-acetamidoanilides of L-arginine,p-guanidino-L-phenylalanine, L-lysine, N2-[D-fructos-3-O-yl and D-glucos-3-O-yl]acetyl-L-lysine as potential acrosin inhibitors
  作者：R.Alan Chrusciel、Ludwig Bauer、JoAnne M. Kaminski、Lourens J.D. Zaneveld

  DOI：10.1016/s0040-4020(01)80998-4

  日期：1991.10

  Syntheses of 4-acetamidophenyl esters and 4-acetamidoanilides of L-lysine,p-guanidino-L-phenylalanine, L-leucyl-L-lysine, L-leucyl-L-leucyl-L-lysine, N2-[(1,2-O-isopropylidene-alpha-D-glucofuranos-3-O-yl)acetyl]-L-lysine, N2-[(1,2-O-isopropylidene-beta-D-fructopyranos-3-O-yl)acetyl]-L-lysine are reported. 4-Acetamidophenyl L-argininate was too unstable to be isolated but L-arginin-4-acetamidoanilide was prepared. These amino acid and peptide derivatives proved to be enantiomerically pure and were characterized by their H-1 and C-13 chemical shifts which were established by means of multipulse 1D and 2D NMR techniques. Preliminary evaluation showed these compounds to be relatively weak inhibitors of human acrosin and bovine trypsin.
• Bicyclic nucleoside analogues from d-glucose: synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives
  作者：Subhankar Tripathi、Joy Krishna Maity、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.carres.2005.02.007

  日期：2005.5

  The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a D-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3 '-O, and 5 '-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the D-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues. (c) 2005 Elsevier Ltd All rights reserved.
• Synthesis of 3-O-(2-iodoethyl)-d-glucose, a stable iodo derivative of d-glucose for medical imaging
  作者：Gilles Bignan、Christophe Morin、Michel Vidal

  DOI：10.1016/0008-6215(93)84144-u

  日期：1993.10