(1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

Base Information

• Chemical Name: (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol
• CAS No.: 693245-47-5
• Molecular Formula: C₁₉H₂₅NO₆
• Molecular Weight: 363.411

Synonyms:(1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

Chemical Property of (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

Chemical Property:

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Technology Process of (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

There total 4 articles about (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol 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: 76.0%

acetic anhydride (108-24-7) + (1S,2S,4R,7S,9S,10S)-9-azido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7-ol (693245-46-4) → (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7-ol (693245-47-5)

Guidance literature:

With hydrogen; nickel; In ethanol; at 20 ℃; for 3h; atmospheric pressure;

DOI:10.1039/b314795a

Reference yield:

(1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7,9-diol (693245-41-9) → (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7-ol (693245-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine; DMAP / 16 h / 20 °C

2: 88 percent / NaN₃ / dimethylformamide / 14 h / 120 °C

3: 76 percent / H₂ / Raney nickel / ethanol / 3 h / 20 °C / atmospheric pressure

With pyridine; dmap; sodium azide; hydrogen; nickel; In ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b314795a

Reference yield:

1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol (694527-29-2) → (1S,2S,4R,7S,9S,10S)-9-acetamido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.02,7]tridecane-7-ol (693245-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOMe / methanol / 1 h / 20 °C

1.2: 59 percent / p-TsOH*H₂O / dimethylformamide / 3 h / 50 °C

2.1: 41 percent / TsOH*H₂O / dimethylformamide / 4 h / 20 °C

3.1: 100 percent / pyridine; DMAP / 16 h / 20 °C

4.1: 88 percent / NaN₃ / dimethylformamide / 14 h / 120 °C

5.1: 76 percent / H₂ / Raney nickel / ethanol / 3 h / 20 °C / atmospheric pressure

With pyridine; dmap; sodium azide; hydrogen; sodium methylate; toluene-4-sulfonic acid; nickel; In methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1039/b314795a

upstream raw materials:

acetic anhydride

(1S,2S,4R,7S,9S,10S)-9-azido-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7-ol

(1S,2S,4R,7S,9R,10S)-12,12-dimethyl-4-phenyl-3,5,11,13-tetra-oxatricyclo[8.3.0.0^2,7]tridecane-7,9-diol

1L-(1,2,4/3,5)-1-C-(acetoxymethyl)-2,3,4,5-tetra-O-acetyl-1,2,3,4,5-cyclohexanepentol

Downstream raw materials:

(1S,2S,3R,4S,5S)-1-amino-5-hydroxymethyl-2,3,4,5-tetrahydroxycyclohexane

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