(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

Base Information

• Chemical Name: (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester
• CAS No.: 955376-11-1
• Molecular Formula: C₅₉H₇₂N₂O₁₃
• Molecular Weight: 1017.23
• Mol file: 955376-11-1.mol

Synonyms:(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

Chemical Property of (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

There total 11 articles about (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl 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:

α-methyl N-(tert-butoxycarbonyl)aspartate (98045-03-5,137130-65-5) → (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester (955376-11-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 4-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.17 h / -15 °C

1.2: NaBH₄ / tetrahydrofuran; H₂O / 0.17 h / -10 °C

2.1: 347 mg / molecular sieves 4 Angstroem; pyridinium chlorochromate / CH₂Cl₂ / 0.75 h

3.1: 38 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 0 °C

4.1: 45 percent / molecular sieves 4 Angstroem / 2-methyl-propan-2-ol / 24 h / 70 °C

5.1: 320 mg / pyridinium chlorochromate immobilized on silica gel / CH₂Cl₂ / 12 h / 20 °C

6.1: LiOH / tetrahydrofuran; H₂O / 1 h

With 4-methyl-morpholine; lithium hydroxide; 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium chlorochromate; isobutyl chloroformate; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo071221r

Reference yield:

(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester (955376-03-1) → (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester (955376-11-1)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; for 1h;

DOI:10.1021/jo071221r

Reference yield:

tert-butyl 3-aminocrotonate → (2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-carboxyethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester (955376-11-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 45 percent / molecular sieves 4 Angstroem / 2-methyl-propan-2-ol / 24 h / 70 °C

2: 320 mg / pyridinium chlorochromate immobilized on silica gel / CH₂Cl₂ / 12 h / 20 °C

3: LiOH / tetrahydrofuran; H₂O / 1 h

With lithium hydroxide; 4 A molecular sieve; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo071221r

upstream raw materials:

(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-3,5-dicarboxylic acid di-tert-butyl ester

(2'''S)-4-((2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl)-2-(2'''-(tert-butoxycarbonylamino)-2'''-(methoxycarbonyl)ethyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylic acid di-tert-butyl ester

(2S)-6-tert-butyl 1-methyl 2-(tert-butoxycarbonylamino)-4-oxohexanedioate

α-methyl N-(tert-butoxycarbonyl)aspartate

Downstream raw materials:

C₅₉H₇₂N₂O₁₂NCHC₇H₇CO₂C₂H₅

Refernces