methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate

Base Information

• Chemical Name: methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate
• CAS No.: 850354-00-6
• Molecular Formula: C₈H₁₄O₅
• Molecular Weight: 191.188
• Mol file: 850354-00-6.mol

Synonyms:methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate

Chemical Property of methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate

There total 10 articles about methyl (2R)-[2-⁽²⁾H₁]-5-deoxyquinate 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: 69.0%

(1R,2R,3R,4S)-[2-(2)H1]-3,4-O-isopropylidene-1-hydroxymethyl-1-hydroxycyclohexan-3,4-diol (850353-91-2) + methanol (67-56-1) → methyl (2R)-[2-(2)H1]-5-deoxyquinate (850354-00-6)

Guidance literature:

(1R,2R,3R,4S)-[2-⁽²⁾H₁]-3,4-O-isopropylidene-1-hydroxymethyl-1-hydroxycyclohexan-3,4-diol; methanol; With oxygen; sodium hydrogencarbonate; platinum; In water; at 55 ℃; for 16h;

With Amberlite IR-120 (H+); In methanol; for 16h; Heating;

DOI:10.1016/j.tetlet.2005.01.134

Reference yield:

methyl 3,4-O-isopropylidene-5-O-thiocarbonylimidazoleshikimate (850353-80-9) → methyl (2R)-[2-(2)H1]-5-deoxyquinate (850354-00-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / Bu₃SnH; AIBN / toluene / 3 h / Heating

2: 79 percent / Amberlite IR-120 (H⁺) / methanol / 16 h / Heating

3: 57 percent / t-BuOOH; V(acac)3 / CH₂Cl₂ / 24 h / 20 °C

4: 100 percent / (+/-)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

5: 92 percent / NaBH₄ / tetrahydrofuran / 14 h / 20 °C

6: 83 percent / LiAlD₄ / diethyl ether / 5 h / -78 °C

7: O₂; NaHCO₃ / Pt / acetone; H₂O / 16 h / 55 °C / atmospheric pressure

8: 149 mg / Amberlite IR-120 (H⁺) / 16 h / Heating

With tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium deuteride; vanadium trisacetylacetonate; 2,2'-azobis(isobutyronitrile); Amberlite IR-120 (H⁺); camphor-10-sulfonic acid; oxygen; tri-n-butyl-tin hydride; sodium hydrogencarbonate; platinum; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene;

DOI:10.1039/b515937g

Reference yield:

methyl (1R,2S)-3,4-O-isopropylidene-1,2-epoxy-5-deoxyshikimate (850353-82-1) → methyl (2R)-[2-(2)H1]-5-deoxyquinate (850354-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / NaBH₄ / tetrahydrofuran / 14 h / 20 °C

2: 83 percent / LiAlD₄ / diethyl ether / 5 h / -78 °C

3: O₂; NaHCO₃ / Pt / acetone; H₂O / 16 h / 55 °C / atmospheric pressure

4: 149 mg / Amberlite IR-120 (H⁺) / 16 h / Heating

With sodium tetrahydroborate; lithium aluminium deuteride; Amberlite IR-120 (H⁺); oxygen; sodium hydrogencarbonate; platinum; In tetrahydrofuran; diethyl ether; water; acetone;

DOI:10.1039/b515937g

upstream raw materials:

(1R,2R,3R,4S)-[2-⁽²⁾H₁]-3,4-O-isopropylidene-1-hydroxymethyl-1-hydroxycyclohexan-3,4-diol

methanol

methyl (1R,2S)-3,4-O-isopropylidene-1,2-epoxy-5-deoxyshikimate

methyl (1R,2S)-1,2-epoxy-5-deoxyshikimate

Refernces

• 1、 Tavassoli, Ali,Duffy, James E.S.,Young, Douglas W.. "Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-2H 1]-homocitrates and the corresponding dimethyl ester lactones-towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein". . p. 2093 - 2096. Retrieved 2007/10/03.