(3aS,4S,6R,6aR)-6-Methoxy-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester | 162254-50-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6R,6aR)-6-Methoxy-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
• 英文别名: methyl (3aS,4S,6R,6aR)-6-methoxy-2,2,4-trimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxole-4-carboxylate
• CAS: 162254-50-4
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: FXXWOIBGKHXNDC-UVMAFCGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aR)-6-Methoxy-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester 在 盐酸 、 锂硼氢 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (2S)-4-[[(2S,3S,4R,5R)-3,4-dihydroxy-5-methoxy-2-methyloxolan-2-yl]methylsulfanyl]-2-[(2,2,2-trifluoroacetyl)amino]butanoate
  参考文献：
  名称：

  Chemoenzymic Synthesis of 4-Substituted Riboses. S-(4'-Methyladenosyl)-L-homocysteine

  摘要：

  The synthesis of 4-C-methyl-D-ribose, 4-C-methyl-D-ribose, D-ribose-4-d, and L-ribose derivatives as well as the title nucleoside by a chemoenzymatic strategy beginning from cyclopentadiene is described.

  DOI：

  10.1021/jo00099a005
• 作为产物：
  描述：

  (3αS,4R,6S,6αR)-4β-acetoxy-2,2-dimethyl-6-hydroxy-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxole 在 吡啶 、 重铬酸吡啶 、 二甲基硫 、 4 A molecular sieve 、 溴 、 对甲苯磺酸 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 生成 (3aS,4S,6R,6aR)-6-Methoxy-2,2,4-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  Chemoenzymic Synthesis of 4-Substituted Riboses. S-(4'-Methyladenosyl)-L-homocysteine

  摘要：

  The synthesis of 4-C-methyl-D-ribose, 4-C-methyl-D-ribose, D-ribose-4-d, and L-ribose derivatives as well as the title nucleoside by a chemoenzymatic strategy beginning from cyclopentadiene is described.

  DOI：

  10.1021/jo00099a005

文献信息

• Search for New Purine- and Ribose-Modified Adenosine Analogs as Selective Agonists and Antagonists at Adenosine Receptors
  作者：Suhaib M. Siddiqi、Kenneth A. Jacobson、John L. Esker、Mark E. Olah、Xiao-duo Ji、Neli Melman、Kamal N. Tiwari、John A. Secrist、Stewart W. Schneller

  DOI：10.1021/jm00007a014

  日期：1995.3

  The binding affinities at rat A(1), A(2a), and A(3) adenosine receptors of a wide range of derivatives of adenosine have been determined. Sites of modification include the purine moiety (1-, 3-, and 7-deaza; halo, alkyne, and amino substitutions at the 2- and 8-positions; and N6(-)CH(2)-ring, -hydrazino, and -hydroxylamino) and the ribose moiety (2'-, 3'-, and 5'-deoxy; 2'- and 3'-O-methyl;2'-deoxy 2'-fluoro;6'-thio;5'-uronamide;carbocyclic;4'- or 3'-methyl; and inversion of configuration. (-)- and (+)-5'-Noraristeromycin were 48- and 21-fold selective, respectively, for A(2a), vs A(1) receptors. 2-Chloro-6'-thioadenosine displayed a K-i value of 20 nM at A(2a) receptors (15-fold selective vs A(1)). 2-Chloroadenin-9-yl(beta-L-2'-deoxy-6'-thiolyxofuranoside) displayed a K-i value of 8 mu M at A(1) receptors and appeared to be an antagonist, on the basis of the absence of a GTP-induced shift in binding vs a radiolabeled antagonist (8-cyclopentyl-1,3-dipropylxanthine). 2-Chloro-2'-deoxyadenosine and 2-chloroadenin-9-yl(beta-D-6'-thioarabinoside) were putative partial agonists at A(1) receptors, with K-i values of 7.4 and 5.4 mu M, respectively. The A(2a) selective agonist 2-(1-hexynyl)-5'-(N-ethylcarbamoyl)adenosine displayed a K-i value of 26 nM at A(3) receptors. The 4'-methyl substitution of adenosine was poorly tolerated, yet when combined with other favorable modifications, potency was restored. Thus, N-6-benzyl-4'methyladenosine-5'-(N-methyluronamide) displayed a K-i value of 604 nM at A(3) receptors and was 103- and 88-fold selective vs A(1) and A(2a) receptors, respectively. This compound was a full agonist in the A(3)-mediated inhibition of adenylate cyclase in transfected CHO cells. The carbocyclic analogue of N-6-(3-iodobenzyl)adenosine-5'-(N-methyluronamide) was 2-fold selective for A(3) VS A(1) receptors and was nearly inactive at A(2a) receptors.
• Chemoenzymic Synthesis of 4-Substituted Riboses. S-(4'-Methyladenosyl)-L-homocysteine
  作者：Carl R. Johnson、John L. Esker、Michael C. Van Zandt

  DOI：10.1021/jo00099a005

  日期：1994.10

  The synthesis of 4-C-methyl-D-ribose, 4-C-methyl-D-ribose, D-ribose-4-d, and L-ribose derivatives as well as the title nucleoside by a chemoenzymatic strategy beginning from cyclopentadiene is described.