2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 387881-19-8
• Molecular Formula: C₄₉H₇₀N₃O₂₁PSi
• Molecular Weight: 1096.16
• Mol file: 387881-19-8.mol

Synonyms:2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property of 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester

There total 13 articles about 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl 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:

2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphanyloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester → 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester (387881-19-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -40 - 20 ℃; for 1h;

DOI:10.1021/ja0166848

Reference yield:

2-(2-{2-acetoxymethyl-5-acetylamino-6-benzyloxy-3-[4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-trimethylsilanyl-ethyl ester (387881-18-7) → 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester (387881-19-8)

Guidance literature:

Multi-step reaction with 5 steps

1: diaminoethylene-derivatized Merrifield resin; 4 Angstroem sieves / butan-1-ol / 24 h / 85 °C

2: 1.58 g / pyridine / 20 °C

3: 93 percent / H₂ / 10percent Pd/C / methanol / 1 h

4: tetrazole / CH₂Cl₂ / 1 h / -30 - 20 °C

5: 0.95 g / m-CPBA / CH₂Cl₂ / 1 h / -40 - 20 °C

With pyridine; 1H-tetrazole; 4 A molecular sieve; diaminoethylene-derivatized Merrifield resin; hydrogen; 3-chloro-benzenecarboperoxoic acid; 10percent Pd/C; In methanol; dichloromethane; butan-1-ol;

DOI:10.1021/ja0166848

Reference yield:

(S)-2-[(R)-2-((2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-hydroxy-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester (387881-17-6) → 2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-trimethylsilanyl-ethyl ester (387881-19-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / silver triflate / CH₂Cl₂ / -40 - 20 °C

2: diaminoethylene-derivatized Merrifield resin; 4 Angstroem sieves / butan-1-ol / 24 h / 85 °C

3: 1.58 g / pyridine / 20 °C

4: 93 percent / H₂ / 10percent Pd/C / methanol / 1 h

5: tetrazole / CH₂Cl₂ / 1 h / -30 - 20 °C

6: 0.95 g / m-CPBA / CH₂Cl₂ / 1 h / -40 - 20 °C

With pyridine; 1H-tetrazole; 4 A molecular sieve; diaminoethylene-derivatized Merrifield resin; hydrogen; silver trifluoromethanesulfonate; 3-chloro-benzenecarboperoxoic acid; 10percent Pd/C; In methanol; dichloromethane; butan-1-ol;

DOI:10.1021/ja0166848

upstream raw materials:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide

(S)-Alanin-(2-trimethylsilylethyl)ester

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

(S)-2-[(R)-2-((2S,3R,4R,5S,6R)-3-Acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-propionylamino]-propionic acid 2-trimethylsilanyl-ethyl ester

Downstream raw materials:

(S)-2-{(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid