8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂

Base Information

• Chemical Name: 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂
• CAS No.: 205050-45-9
• Molecular Formula: C₃₇H₄₃BrN₄O₆Si
• Molecular Weight: 747.761

Synonyms:8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂

Chemical Property of 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂

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Technology Process of 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂

There total 8 articles about 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B₂ 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: 61.0%

aniline (62-53-3) + 8-O-(tert-butyldimethylsilyl)-2-methyl-3-carboxy-A-ring-pyrrole-duocarmicyn B2 (205051-58-7) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B2 (205050-45-9)

Guidance literature:

With diethyl chlorophosphate; triethylamine; In tetrahydrofuran; a) 0 deg C, 1 h, b) RT, 12 h;

DOI:10.1021/jm990094r

Reference yield:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B2 (205050-45-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.70 g / K₂CO₃ / 5.67 h / 0 °C

2: 35 percent / NaBH₄ / various solvent(s) / 105 h / 0 °C

3: 71 percent / BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

4: 99 percent / Pd(PPh₃)4, dimedone / tetrahydrofuran / 1 h / Ambient temperature

5: 61 percent / DECP, Et₃N / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 12 h

With sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trifluoride diethyl etherate; potassium carbonate; diethyl chlorophosphate; dimedone; triethylamine; In tetrahydrofuran; chloroform;

DOI:10.1021/jm990094r

Reference yield:

8-bromomethyl-4-(tert-butyl-dimethyl-silanyloxy)-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydro-3,6-diaza-as-indacene-2-carboxylic acid benzyl ester → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(N-phenylcarbamoyl)-A-ring-pyrrole-duocarmycyn B2 (205050-45-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 35 percent / NaBH₄ / various solvent(s) / 105 h / 0 °C

2: BF₃*Et₂O / CHCl₃ / 17.5 h / Ambient temperature

3: 80 percent / 25 percent aq. HCO₂NH₄ / 10 percent Pd/C / tetrahydrofuran / 0.5 h / Ambient temperature

4: 61 percent / DECP, Et₃N / tetrahydrofuran / a) 0 deg C, 1 h, b) RT, 12 h

With sodium tetrahydroborate; boron trifluoride diethyl etherate; ammonium formate; diethyl chlorophosphate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; chloroform;

DOI:10.1021/jm990094r

upstream raw materials:

aniline

8-O-(tert-butyldimethylsilyl)-2-methyl-3-carboxy-A-ring-pyrrole-duocarmicyn B₂

8-O-tert-butyldimethylsilylduocarmycin B₂

8-O-(tert-butyldimethylsilyl)-2-methyl-3-(allyloxycarbonyl)-A-ring-pyrrole-duocarmycin B₂

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