(3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutaMic Acid

Base Information

• Chemical Name: (3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutaMic Acid
• CAS No.: 910548-26-4
• Molecular Formula: C₁₁H₁₉NO₆
• Molecular Weight: 261.275
• Mol file: 910548-26-4.mol

Synonyms:(2S,3R)-N-tert-butoxycarbonyl-3-methylglutamic acid

Chemical Property of (3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutaMic Acid

Chemical Property:

• Solubility.: Dichloromethane, Methanol

Purity/Quality:

(3R)-N-(tert-Butyloxycarbonyl)-3-methyl-L-glutamicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutamic Acid can be used in the preparation of (2S,3R)-3-Me glutamate residue of nonribosomal lipopeptides.

Technology Process of (3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutaMic Acid

There total 8 articles about (3R)-N-(tert-Butyloxycarbonyl)-3-Methyl-L-glutaMic Acid 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%

(2S,3R)-N-tert-butyloxycarbonyl-3-methylpyroglutamic acid (910548-25-3) → (2S,3R)-N-tert-butoxycarbonyl-3-methylglutamic acid (910548-26-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 18h;

DOI:10.1021/ja062960c

Reference yield:

(3R,4R,5S)-5-tert-butyldiphenylsilyloxymethyl-N-tert-butyloxycarbonyl-3,4-pyrazolinepyrrolidin-2-one (910548-23-1) → (2S,3R)-N-tert-butoxycarbonyl-3-methylglutamic acid (910548-26-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 42 percent / 3 h / 120 °C

2: 80 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 20 °C

3: 73 percent / TBAF / tetrahydrofuran; acetic acid; H₂O / 0 - 20 °C

4: 70 percent / RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O / 3 h / 20 °C

5: 69 percent / LiOH / H₂O; tetrahydrofuran / 18 h / 20 °C

With ruthenium trichloride; lithium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; platinum(IV) oxide; In tetrahydrofuran; tetrachloromethane; water; acetic acid; ethyl acetate; acetonitrile;

DOI:10.1021/ja062960c

Reference yield:

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (138871-58-6) → (2S,3R)-N-tert-butoxycarbonyl-3-methylglutamic acid (910548-26-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 68 percent / diethyl ether / 72 h / 20 °C

2: 42 percent / 3 h / 120 °C

3: 80 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 20 °C

4: 73 percent / TBAF / tetrahydrofuran; acetic acid; H₂O / 0 - 20 °C

5: 70 percent / RuCl₃; NaIO₄ / acetonitrile; CCl₄; H₂O / 3 h / 20 °C

6: 69 percent / LiOH / H₂O; tetrahydrofuran / 18 h / 20 °C

With ruthenium trichloride; lithium hydroxide; sodium periodate; tetrabutyl ammonium fluoride; hydrogen; platinum(IV) oxide; In tetrahydrofuran; tetrachloromethane; diethyl ether; water; acetic acid; ethyl acetate; acetonitrile;

DOI:10.1021/ja062960c

upstream raw materials:

(2S,3R)-N-tert-butyloxycarbonyl-3-methylpyroglutamic acid

(4R,5S)-N-tert-butyloxycarbonyl-5-hydroxymethyl-4-methylpyrrolidin-2-one

(3R,4R,5S)-5-tert-butyldiphenylsilyloxymethyl-N-tert-butyloxycarbonyl-3,4-pyrazolinepyrrolidin-2-one

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3R)-3-methylglutamic acid hydrochloride

Refernces