2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester

Base Information

• Chemical Name: 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester
• CAS No.: 864239-06-5
• Molecular Formula: C₂₇H₄₅NO₅
• Molecular Weight: 463.658
• Mol file: 864239-06-5.mol

Synonyms:2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester

Chemical Property of 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester

There total 4 articles about 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester 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%

2,2-dimethylpropionic acid (5S)-tert-butoxycarbonylamino-(4S)-hydroxy-(2R),7-dimethyloctyl ester (864239-05-4) + benzyl bromide (100-39-0) → 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester (864239-06-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 14h;

DOI:10.1021/jm050142+

Reference yield:

pivaloyl chloride (3282-30-2) → 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester (864239-06-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

2: 69 percent / n-Bu₄NI; NaH / tetrahydrofuran / 14 h / 20 °C

With pyridine; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm050142+

Reference yield:

(3R,5S,1'S)-5-[1'-[(tert-butyloxycarbonyl)amino]-3'-methylbutyl]-3-methyldihydrofuran-2(3H)-one (169057-47-0) → 2,2-dimethylpropionic acid (4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctyl ester (864239-06-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / NaBH₄ / methanol / 1 h / 20 °C

2: 79 percent / pyridine / CH₂Cl₂ / 0 - 20 °C

3: 69 percent / n-Bu₄NI; NaH / tetrahydrofuran / 14 h / 20 °C

With pyridine; sodium tetrahydroborate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm050142+

upstream raw materials:

2,2-dimethylpropionic acid (5S)-tert-butoxycarbonylamino-(4S)-hydroxy-(2R),7-dimethyloctyl ester

benzyl bromide

pivaloyl chloride

(3R,5S,1'S)-5-[1'-[(tert-butyloxycarbonyl)amino]-3'-methylbutyl]-3-methyldihydrofuran-2(3H)-one

Downstream raw materials:

(4S)-benzyloxy-(5S)-tert-butoxycarbonylamino-(2R),7-dimethyloctanoic acid

(S)-2-((2R,4S,5S)-4-Benzyloxy-5-tert-butoxycarbonylamino-2,7-dimethyl-octanoylamino)-propionic acid benzyl ester

(S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-tert-butoxycarbonylamino-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester

(S)-2-{(2R,4S,5S)-4-Benzyloxy-5-[(S)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-(trityl-carbamoyl)-propionylamino]-2,7-dimethyl-octanoylamino}-propionic acid benzyl ester