Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester
• CAS No.: 229024-84-4
• Molecular Formula: C₃₆H₄₆N₄O₁₆
• Molecular Weight: 790.778

Synonyms:

Chemical Property of Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-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:

methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside (77398-20-0) → Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester (229024-84-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 83 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

2: 5 percent HCl / tetrahydrofuran; H₂O / 1 h / 75 °C

3: imidazole / CH₂Cl₂ / 15 h / 5 °C

4: 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

5: 0.4 equiv. TMSOTf / CH₂Cl₂ / 10.25 h / -70 - 5 °C

With 1H-imidazole; hydrogenchloride; dmap; trimethylsilyl trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; dichloromethane; water; 1: Acylation / 2: Hydrolysis / 3: silylation / 4: Acetylation / 5: glycosylation;

DOI:10.1016/S0040-4039(99)00862-X

Reference yield:

((2S,3S,4S,6S)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-carbamic acid 4-nitro-benzyl ester (229024-81-1) → Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester (229024-84-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 5 percent HCl / tetrahydrofuran; H₂O / 1 h / 75 °C

2: imidazole / CH₂Cl₂ / 15 h / 5 °C

3: 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

4: 0.4 equiv. TMSOTf / CH₂Cl₂ / 10.25 h / -70 - 5 °C

With 1H-imidazole; hydrogenchloride; dmap; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; water; 1: Hydrolysis / 2: silylation / 3: Acetylation / 4: glycosylation;

DOI:10.1016/S0040-4039(99)00862-X

Reference yield:

((2S,3S,4S)-3,6-Dihydroxy-2-methyl-tetrahydro-pyran-4-yl)-carbamic acid 4-nitro-benzyl ester → Acetic acid (2S,3S,4S,6R)-6-{4-[(2R,4S,5S,6S)-5-acetoxy-6-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-2-yloxy]-butoxy}-2-methyl-4-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-3-yl ester (229024-84-4)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / CH₂Cl₂ / 15 h / 5 °C

2: 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

3: 0.4 equiv. TMSOTf / CH₂Cl₂ / 10.25 h / -70 - 5 °C

With 1H-imidazole; dmap; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; 1: silylation / 2: Acetylation / 3: glycosylation;

DOI:10.1016/S0040-4039(99)00862-X

upstream raw materials:

methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside

((2S,3S,4S,6S)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-carbamic acid 4-nitro-benzyl ester

4-nitrobenzyl chloroformate

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