methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate

Base Information

• Chemical Name: methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate
• CAS No.: 100235-80-1
• Molecular Formula: C₁₄H₁₆N₂O₈
• Molecular Weight: 340.29
• Mol file: 100235-80-1.mol

Synonyms:

Chemical Property of methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate

There total 2 articles about methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate 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:

methyl (S)-3-hydroxyvalerate (42558-50-9) → 3,5-Dinitro-benzoic acid (1S,2R)-1-ethyl-2-methoxycarbonyl-propyl ester (100235-80-1,100235-84-5,109619-92-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi, (i-Pr)2NH / 1.) hexane, THF, 0 deg C, 1h, 2.) -60 deg C, THF, then -30 deg C, 30 min, then HMPA, -30 deg C, 45 min

2: DCC, DMAP / CH₂Cl₂ / 0 degC, then room temp.

With dmap; n-butyllithium; diisopropylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1016/S0040-4020(01)82049-4

Reference yield:

3,5-dinitrobenzoic acid (99-34-3) + methyl (3R)-3-hydroxypentanoate (42558-50-9,56009-31-5,60793-22-8,133098-13-2) → methyl (3R)-3-(3',5'-dinitrobenzoyloxy)-pentanoate (95338-08-2) + methyl (2S,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate + methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate (100235-80-1)

Guidance literature:

With dicyclohexyl-carbodiimide; dmap; Multistep reaction; 2.) dichloromethane, 3 h, room temp.;

Reference yield:

methyl (2R,3R)-3-(3',5'-dinitrobenzoyloxy)-2-methylpentanoate (100235-80-1) → (2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentyl tosylate (100296-86-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 82.9 percent / aq. KOH; tetrahydrofuran; methanol / 2 h / 0 °C

2: 99.8 percent

3: 97.8 percent

4: 93.3 percent / pyridine / 0 °C

With pyridine; In tetrahydrofuran; methanol; potassium hydroxide;

upstream raw materials:

methyl (S)-3-hydroxyvalerate

3,5-dinitrobenzoic acid

methyl (3R)-3-hydroxypentanoate

Downstream raw materials:

(2S,3R)-2-methyl-3-tetrahydropyranyloxy-1-pentyl tosylate

Refernces

• 1、 Kato, Minoru,Mori, Kenji. "Synthesis of (3R,4S)-4-Methyl-3-hexanol, the Pheromone of the Ant Tetramorium impurum". . p. 3073 - 3076. Retrieved 2007/10/02.