methyl 5-deoxy-[2-⁽²⁾H]-shikimate

Base Information

• Chemical Name: methyl 5-deoxy-[2-⁽²⁾H]-shikimate
• CAS No.: 850353-88-7
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 173.173
• Mol file: 850353-88-7.mol

Synonyms:methyl 5-deoxy-[2-⁽²⁾H]-shikimate

Chemical Property of methyl 5-deoxy-[2-⁽²⁾H]-shikimate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-deoxy-[2-⁽²⁾H]-shikimate

There total 3 articles about methyl 5-deoxy-[2-⁽²⁾H]-shikimate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

methyl 3,4-O-isopropylidene-5-deoxy-[2-(2)H]-shikimate (850353-87-6) → methyl 5-deoxy-[2-(2)H]-shikimate (850353-88-7)

Guidance literature:

With Amberlite IR-120 (H+); In methanol; for 3h; Heating;

DOI:10.1016/j.tetlet.2005.01.134

Reference yield:

methyl 3,4-O-isopropylidene-[2-(2)H]-shikimate (850353-85-4) → methyl 5-deoxy-[2-(2)H]-shikimate (850353-88-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂ / 16 h / 20 °C

2: 80 percent / Bu₃SnH; AIBN / toluene / 3 h / Heating

3: 80 percent / Amberlite IR-120 (H⁺) / methanol / 16 h / Heating

With 2,2'-azobis(isobutyronitrile); Amberlite IR-120 (H⁺); tri-n-butyl-tin hydride; In methanol; dichloromethane; toluene;

DOI:10.1039/b515937g

Reference yield:

methyl 3,4-O-isopropylidene-5-O-thiocarbonylimidazole-[2-(2)H]-shikimate (850353-86-5) → methyl 5-deoxy-[2-(2)H]-shikimate (850353-88-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / Bu₃SnH; AIBN / toluene / 3 h / Heating

2: 80 percent / Amberlite IR-120 (H⁺) / methanol / 16 h / Heating

With 2,2'-azobis(isobutyronitrile); Amberlite IR-120 (H⁺); tri-n-butyl-tin hydride; In methanol; toluene;

DOI:10.1039/b515937g

upstream raw materials:

methyl 3,4-O-isopropylidene-5-deoxy-[2-⁽²⁾H]-shikimate

methyl 3,4-O-isopropylidene-[2-⁽²⁾H]-shikimate

methyl 3,4-O-isopropylidene-5-O-thiocarbonylimidazole-[2-⁽²⁾H]-shikimate

Downstream raw materials:

methyl (2S)-[2-⁽²⁾H₁]-5-deoxyquinate

Refernces

• 1、 Tavassoli, Ali,Duffy, James E. S.,Young, Douglas W.. "Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H 1]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2- 2H1]-homocitrate lactones - An assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V protein". . p. 569 - 580. Retrieved 2008/02/02.