Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester
• CAS No.: 214473-46-8
• Molecular Formula: C₃₂H₄₀N₄O₁₁
• Molecular Weight: 656.69

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester

There total 9 articles about Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl 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-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-galactopyranosyl azide → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester (214473-46-8)

Guidance literature:

Multi-step reaction with 8 steps

1: hydrogen / platinum oxide / ethanol / 5 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 0 deg C, 1 h, then room temp., 16 h

3: ammonia / methanol / 6 h / 0 °C

4: pyridine / 0 deg C, 1 h, then room temp., 16 h

5: 75 percent / sodium azide / dimethylformamide / 16 h / 80 °C

6: triphenylphosphine / tetrahydrofuran; H₂O / 3 h / Heating

7: tetrahydrofuran; H₂O / 3 h / Ambient temperature

8: pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; sodium azide; ammonia; hydrogen; triphenylphosphine; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00011-1

Reference yield:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester (214473-46-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 0 deg C, 1 h, then room temp., 16 h

2: ammonia / methanol / 6 h / 0 °C

3: pyridine / 0 deg C, 1 h, then room temp., 16 h

4: 75 percent / sodium azide / dimethylformamide / 16 h / 80 °C

5: triphenylphosphine / tetrahydrofuran; H₂O / 3 h / Heating

6: tetrahydrofuran; H₂O / 3 h / Ambient temperature

7: pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; sodium azide; ammonia; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00011-1

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-5-acetylamino-6-benzyloxycarbonylamino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-4-yl ester (214473-46-8)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 0 deg C, 1 h, then room temp., 16 h

2: ammonia / methanol / 6 h / 0 °C

3: pyridine / 0 deg C, 1 h, then room temp., 16 h

4: 75 percent / sodium azide / dimethylformamide / 16 h / 80 °C

5: triphenylphosphine / tetrahydrofuran; H₂O / 3 h / Heating

6: tetrahydrofuran; H₂O / 3 h / Ambient temperature

7: pyridine / CH₂Cl₂ / 6 h / Ambient temperature

With pyridine; sodium azide; ammonia; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00011-1

upstream raw materials:

acetic anhydride

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

benzyl chloroformate

((2R,3R,4R,5S,6R)-3-Acetylamino-6-azidomethyl-4,5-dihydroxy-tetrahydro-pyran-2-yl)-carbamic acid benzyl ester

Downstream raw materials:

(S)-2-((S)-2-Benzoylamino-3-{(2R,3R,4R,5R,6R)-4,5-diacetoxy-3-acetylamino-6-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-2-ylcarbamoyl}-propionylamino)-3-(4-hydroxy-3-nitro-phenyl)-propionic acid methyl ester

Acetic acid (2R,3R,4R,5R,6R)-4-acetoxy-5-acetylamino-6-amino-2-[(2-tert-butoxycarbonylamino-benzoylamino)-methyl]-tetrahydro-pyran-3-yl ester

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