4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester

Base Information

• Chemical Name: 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester
• CAS No.: 132446-45-8
• Molecular Formula: C₃₉H₄₇NO₁₃
• Molecular Weight: 737.801

Synonyms:4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester

Chemical Property of 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester

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Technology Process of 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester

There total 5 articles about 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-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: 33.0%

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside (110236-56-1) + 2-O-fluoromethyl-3-O-levulinoyl-(R)-glyceric acid methyl ester (132446-43-6) → 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester (132446-45-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃; for 1h; molecular sieve 4 Angstroem;

DOI:10.1016/S0040-4020(01)81477-0

Reference yield:

2-O-methoxymethyl-(R)-glyceric acid methyl ester (116303-07-2) → 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester (132446-45-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine, N,N-dimethylaminopyridine / 2 h / Ambient temperature

2: 58 percent / acetic acid, trifluoroacetic acid / 2 h / Ambient temperature

3: 70 percent / 70percent HF/pyridine / CH₂Cl₂ / 0 °C

4: 33 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -10 °C / molecular sieve 4 Angstroem

With pyridine; dmap; boron trifluoride diethyl etherate; hydrogen fluoride; acetic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81477-0

Reference yield:

3-O-levulinoyl-2-O-methoxymethyl-(R)-glyceric acid methyl ester (132446-42-5) → 4-Oxo-pentanoic acid (R)-2-((2R,3S,4R,5R,6S)-4-benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-2-methoxycarbonyl-ethyl ester (132446-45-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 58 percent / acetic acid, trifluoroacetic acid / 2 h / Ambient temperature

2: 70 percent / 70percent HF/pyridine / CH₂Cl₂ / 0 °C

3: 33 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -10 °C / molecular sieve 4 Angstroem

With pyridine; boron trifluoride diethyl etherate; hydrogen fluoride; acetic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0040-4020(01)81477-0

upstream raw materials:

methyl N-benzyloxycarbonyl-2-deoxy-3,6-di-O-benzylglucopyranoside

2-O-fluoromethyl-3-O-levulinoyl-(R)-glyceric acid methyl ester

2-O-methoxymethyl-(R)-glyceric acid methyl ester

3-O-levulinoyl-2-O-methoxymethyl-(R)-glyceric acid methyl ester

Downstream raw materials:

(R)-2-((2R,3S,4R,5R,6S)-4-Benzyloxy-5-benzyloxycarbonylamino-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxymethoxy)-3-hydroxy-propionic acid methyl ester

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