Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

Base Information

• Chemical Name: Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester
• CAS No.: 129953-15-7
• Molecular Formula: C32H40 Br N3 O8 Si
• Molecular Weight: 702.6648
• DSSTox Substance ID: DTXSID20926536
• Wikidata: Q76279227
• Mol file: 129953-15-7.mol

Synonyms:129953-15-7;Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester;C32H40BrN3O8Si;DTXSID20926536;C32-H40-Br-N3-O8-Si;LS-34803;Methyl 8-(bromomethyl)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methyl-1-oxo-6-(5,6,7-trimethoxy-1H-indole-2-carbonyl)-1,2,3,6,7,8-hexahydropyrrolo[3,2-e]indole-2-carboxylate

Chemical Property of Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

Chemical Property:

• Vapor Pressure: 1.95E-22mmHg at 25°C
• Boiling Point: 751°Cat760mmHg
• Flash Point: 408°C
• Density: 1.337g/cm³
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 10
• Exact Mass: 701.17680
• Heavy Atom Count: 45
• Complexity: 1150

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)C2=C3C(CN(C3=CC(=C2N1)O[Si](C)(C)C(C)(C)C)C(=O)C4=CC5=CC(=C(C(=C5N4)OC)OC)OC)CBr)C(=O)OC
• Isomeric SMILES: C[C@@]1(C(=O)C2=C3[C@@H](CN(C3=CC(=C2N1)O[Si](C)(C)C(C)(C)C)C(=O)C4=CC5=CC(=C(C(=C5N4)OC)OC)OC)CBr)C(=O)OC

Technology Process of Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl ester

There total 1 articles about Benzo(1,2-b:4,3-b')dipyrrole-2-carboxylic acid, 1,2,3,6,7,8-hexahydro-8-(bromomethyl)-4-(((1,1-dimethylethyl)dimethylsilyl)oxy)-2-methyl-1-oxo-6-((5,6,7-trimethoxy-1H-indol-2-yl)carbonyl)-, methyl 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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + duocarmycin B2 (124325-94-6) → 8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 4.5h; Ambient temperature;

DOI:10.1248/cpb.44.933 DOI:10.1248/cpb.44.1723

Reference yield:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-benzoyl-A-ring-pyrrole-duocarmycin B2 (205050-86-8)

Guidance literature:

Multi-step reaction with 6 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: 60 percent / PhBr / 10 h / 165 °C

6: 51 percent / BF₃*Et₂O / CH₂Cl₂ / 14.6 h / Ambient temperature

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

DOI:10.1021/jm990094r

Reference yield:

8-O-tert-butyldimethylsilylduocarmycin B2 (129953-15-7) → 8-O-(tert-butyldimethylsilyl)-2-methyl-3-(phenylthiocarbonyl)-A-ring-pyrrole-duocarmycyn B2 (205050-80-2)

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

upstream raw materials:

tert-butyldimethylsilyl chloride

duocarmycin B₂

Downstream raw materials:

C₂₂H₂₀N₂O₃

C₂₅H₂₇N₃O₃

4'-methoxycinnamoyl 2-methyl-3-(dimethylaminomethyl)-A-ring-pyrrole-duocarmycin C₂