N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide

Base Information

• Chemical Name: N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide
• CAS No.: 213386-04-0
• Molecular Formula: C₄₃H₅₀N₂O₁₁
• Molecular Weight: 770.877

Synonyms:N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide

Chemical Property of N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide

Chemical Property:

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Technology Process of N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide

There total 8 articles about N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide 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: 35.0%

p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside (213386-03-9) + 2,2,2-Trichloro-acetimidic acid (2S,3R,4R,5S,6S)-5-(benzyl-formyl-amino)-4-benzyloxy-3-methoxy-4,6-dimethyl-tetrahydro-pyran-2-yl ester → N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide (213386-04-0)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; at -30 ℃; for 0.25h;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield:

benzyl bromide (100-39-0) → N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide (213386-04-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / KOH / dimethylformamide / 0.67 h / 0 °C

2: 90 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

3: 90 percent / Bu₄NBr / CH₂Cl₂; aq. NaOH

4: 35 percent / TMSOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / -30 °C

With potassium hydroxide; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; water; trifluoroacetic acid; In sodium hydroxide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00074-3

Reference yield:

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside (80264-82-0) → N-Benzyl-N-{(2S,3S,4R,5R,6S)-4-benzyloxy-6-[(2R,3R,4S,5S,6R)-3-benzyloxy-5-methoxy-2-methyl-6-(4-nitro-phenoxy)-tetrahydro-pyran-4-yloxy]-5-methoxy-2,4-dimethyl-tetrahydro-pyran-3-yl}-formamide (213386-04-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / pyridine / 1.5 h / 60 °C

2: 73 percent / NaI / dimethylformamide / 5 h / 100 °C

3: 53 percent / LiAlH₄ / tetrahydrofuran / 20 h / Ambient temperature

4: 75 percent / KOH / dimethylformamide / 0.67 h / 0 °C

5: 90 percent / CF₃CO₂H, H₂O / CH₂Cl₂ / 0.17 h / Ambient temperature

6: 90 percent / Bu₄NBr / CH₂Cl₂; aq. NaOH

7: 35 percent / TMSOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / -30 °C

With potassium hydroxide; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; tetrabutylammomium bromide; water; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; pyridine; sodium hydroxide; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(98)00074-3

upstream raw materials:

p-nitrophenyl 4-O-benzyl-6-deoxy-2-O-methyl-α-D-mannopyranoside

benzyl bromide

p-nitrophenyl 2,3-O-isopropylidene-α-D-mannopyranoside

p-nitrophenyl 6-deoxy-2,3-O-isopropylidene-α-D-mannopyranoside

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