(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

Base Information

• Chemical Name: (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
• CAS No.: 367276-30-0
• Molecular Formula: C₄₄H₅₈N₃O₂₁P
• Molecular Weight: 995.926
• Mol file: 367276-30-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 23 articles about (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 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: 87.0%

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) → (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 (367276-30-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.75h;

DOI:10.1021/ja0166848

Reference yield:

(S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester (367276-21-9) → (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 (367276-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / H₂ / Pd/C / methanol; tetrahydrofuran / 3 h / 25 °C / 2585.81 Torr

2: 1H-tetrazole / CH₂Cl₂ / 2 h / 25 °C

3: 1.4 g / aq. H₂O₂ / tetrahydrofuran / 2 h / -78 - 20 °C

4: DBU / CH₂Cl₂ / 0.25 h

With 1H-tetrazole; hydrogen; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja017386d

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranosyl bromide (70831-94-6) → (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 (367276-30-0)

Guidance literature:

Multi-step reaction with 7 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

7: 87 percent / TBAF / tetrahydrofuran / 0.75 h / 20 °C

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

DOI:10.1021/ja0166848

upstream raw materials:

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

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-benzenesulfonyl-ethyl ester

dibenzyl N,N-diethylphosphoramidite

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

Downstream raw materials:

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 2,5-dioxo-pyrrolidin-1-yl ester

C₆₅H₉₀F₃N₈O₂₈P