(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester
• CAS No.: 112836-67-6
• Molecular Formula: C₂₄H₂₈N₂O₄
• Molecular Weight: 408.497
• Mol file: 112836-67-6.mol

Synonyms:(S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

Chemical Property of (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester

There total 24 articles about (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl 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: 48.0%

(S)-8-Acetoxymethyl-4-benzyloxy-7,8-dihydro-3H-pyrrolo[3,2-e]indole-1,6-dicarboxylic acid 6-tert-butyl ester 1-methyl ester (176685-39-5) → (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6)

Guidance literature:

With dimethylsulfide borane complex; In tetrahydrofuran; for 19h; Heating;

DOI:10.3987/COM-97-7920

Reference yield:

N5-(Phenylsulfonyl)-5-amino-1-benzoyl-7-(benzyloxy)-3-methylindole (112764-63-3) → (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / conc. sulfuric acid, N-bromosuccinimide / tetrahydrofuran / 1 h / -23 °C

2: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

3: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating

4: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min

5: 83 percent / acetyl chloride / methanol / 2 h / 50 °C

6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C

7: tetrahydrofuran / 20 h / 23 °C

With sodium hydroxide; N-Bromosuccinimide; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; acetyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00222a043

Reference yield:

5-amino-1-benzoyl-7-(benzyloxy)-4-bromo-3-methyl-N5-(phenylsulfonyl)indole (112764-64-4) → (S)-1,6-dihydro-1-(hydroxymethyl)-8-methyl-5-(phenylmethoxy)-benzo[1,2-b:4,3-b']dipyrrole-3(2H)-carboxylic acid 1,1-dimethylethyl ester (112836-67-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) sodium hydride / dimethylformamide / 1.) 25 deg C, 30 min; 2.) 25 deg C, 1 h

2: tri-n-butyltin hydride / AIBN / benzene / 4 h / Heating

3: 1.) borane methyl sulfide 2.) 2 N aq. sodium hydroxide, 30percent aq. hydrogen peroxide / 1.) THF, 25 deg C, 3 h; 2.) THF, 45 deg C, 30 min

4: 83 percent / acetyl chloride / methanol / 2 h / 50 °C

5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 3 h / 100 °C

6: tetrahydrofuran / 20 h / 23 °C

With sodium hydroxide; dimethylsulfide borane complex; dihydrogen peroxide; tri-n-butyl-tin hydride; sodium hydride; acetyl chloride; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00222a043

upstream raw materials:

di-tert-butyl dicarbonate

5-(benzyloxy)-1,2,3,6-tetrahydro-8-methylbenzo<1,2-b:4,3-b'>dipyrrole-1-methanol

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

((S)-5-Benzyloxy-8-methyl-1,2,3,6-tetrahydro-pyrrolo[3,2-e]indol-1-yl)-methanol

Downstream raw materials:

(S)-5-Benzyloxy-1-methanesulfonyloxymethyl-8-methyl-1,6-dihydro-2H-pyrrolo[3,2-e]indole-3-carboxylic acid tert-butyl ester

(+)-N-BOC-CPI

carzelesin

bizelesin

Refernces

• 1、 Hurley,Warpehoski,Lee,McGovren,Scahill,Kelly,Mitchell,Wicnienski,Gebhard,Johnson,Bradford. "Sequence specificity of DNA alkylation by the unnatural enantiomer of CC-1065 and its synthetic analogues". . p. 4633 - 4649. Retrieved 2007/10/02.
• 2、 Boger, Dale L.,Coleman, Robert S.. "Total Synthesis of (+)- and (-)-CPI-CDPI2: (+)-(3bR,4aS)- and (-)-(3bS,4aR)-Deoxy-CC-1065". . p. 695 - 698. Retrieved 2007/10/02.