(S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester
• CAS No.: 177213-16-0
• Molecular Formula: C₄₃H₅₀N₂O₉
• Molecular Weight: 738.878
• Mol file: 177213-16-0.mol

Synonyms:(S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

Chemical Property of (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

There total 8 articles about (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl 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: 92.0%

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) + (2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid (177213-15-9) → (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester (177213-16-0)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.tet.2006.05.080

Reference yield:

(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate (57039-38-0) → (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester (177213-16-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 83 percent / imidazole / dimethylformamide / 2 h / 20 °C

2.1: Ag₂O / dimethylformamide / 20 h / 20 °C

2.2: 7.60 g / acetic acid / H₂O; tetrahydrofuran / 15 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 12 h / 20 °C

4.1: 81 percent / sodium azide / dimethylformamide / 12 h / 20 °C

5.1: 82 percent / LiOH*H₂O / H₂O; methanol; tetrahydrofuran / 12 h / 20 °C

6.1: hydrogen / Lindlar catalyst / methanol / 3 h / 20 °C

7.1: 54 percent / LiOH*H₂O / 12 h / 20 °C

8.1: 92 percent / Et₃N / dimethylformamide / 0 - 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; sodium azide; hydrogen; triethylamine; silver(l) oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.05.080

Reference yield:

(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid (177213-14-8) → (S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester (177213-16-0)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogen / Lindlar catalyst / methanol / 3 h / 20 °C

2: 54 percent / LiOH*H₂O / 12 h / 20 °C

3: 92 percent / Et₃N / dimethylformamide / 0 - 20 °C

With lithium hydroxide; hydrogen; triethylamine; Lindlar's catalyst; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.05.080

upstream raw materials:

methyl (2S)-2-amino-3-phenylpropanoate

(2R,3R,4S,5R,6R)-6-(tert-butoxycarbonylaminomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

(2R,3R,4S,5S,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-(hydroxymethyl)-2H-pyran-2-carboxylate

(2R,3R,4S,5R,6R)-methyl tetrahydro-3,4,5-trihydroxy-6-((tert-butyldimethylsilyloxy)methyl)-2H-pyran-2-carboxylate

Downstream raw materials:

(S)-3-Phenyl-2-{[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-({[(2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butoxycarbonylamino-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-methyl)-tetrahydro-pyran-2-carbonyl]-amino}-propionic acid methyl ester

(S)-2-[((2R,3R,4S,5R,6R)-6-{[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-methyl}-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester

(S)-2-[((2R,3R,4S,5R,6R)-6-Aminomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carbonyl)-amino]-3-phenyl-propionic acid methyl ester