166117-58-4

Upstream product

• 166117-56-2 2′-azido-4′-(benzyloxy)-5′-methoxybenzoic acid 
• 64154-78-5 4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride 
• 140646-99-7 (S)-methyl 1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carboxylate 
• 140693-22-7 (S)-1-(4-(benzyloxy)-5-methoxy-2-nitrobenzoyl)pyrrolidine-2-carbaldehyde 
• 166117-57-3 N-<2-Azido-4-(benzyloxy)-5-methoxybenzoyl>-L-proline methyl ester 
• 166451-17-8 1-[2-azido-4-(benzyloxy)-5-methoxybenzoyl]prolinol 
• 147-85-3 L-proline 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 1248341-69-6 C₂₁H₂₀N₄O₃ 
• 81307-24-6 (11aS)-8-hydroxy-7-methoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one 
• 194783-42-1 (S)-8-Benzyloxy-7,11-dimethoxy-1,2,3,10,11,11a-hexahydro-benzo[e]pyrrolo[1,2-a][1,4]diazepin-5-one 
• 127810-79-1 8-benzyl DC-81 
• 140647-03-6 (2S)-N-(2-amino-4-hydroxy-5-methoxybenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 127810-78-0 (2S)-N-(2-amino-4-benzyloxy-5-methoxybenzoyl)pyrrolidine-2-carbaldehyde diethyl dithioacetal 

Relevant academic research and scientific papers

Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrr

Intramolecular 1,3-dipolar cycloaddition as a route to triazolobenzodiazepines and pyrrolobenzodiazepines

Intramolecular 1,3-dipolar cycloaddition between an alkyne and an azide leads to a series of 1,2,3-triazolo-fused 1,4-benzodiazepines, 1,2,5-benzothiadiazepines, pyrrolobenzodiazepines and pyrrolobenzothiadiazepines (eight examples). The products are priv

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines and their conjugates by azido reductive cyclization strategy as potential DNA-binding agents

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via azido reductive cyclization process employing FeCl3-NaI reagent system. This methodology has been extended for the preparation of new nicotinamido- pyrrolobenzodiazepine hybrids linked through piperazino-alkane-oxy spacers that exhibit good DNA binding affinity.

Synthesis of DNA-interactive pyrrolo[2,1-c][1,4]benzodiazepines by employing polymer-supported reagents: Preparation of DC-81

Polymer-supported reagents have been utilized for the generation of combinatorial library of substituted pyrrolo[2,1-c][1,4]benzodiazepine derivatives that provides a clean and efficient preparation and does not require conventional purification techniques like chromatography. This methodology involves intra molecular aza-Wittig reaction and has been extended for the synthesis of the natural product DC-81 in good overall yields.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via reductive cyclization of ω-Azido carbonyl compounds by TMSI: An efficient preparation of antibiotic DC-81 and its dimers

ω-Azido carbonyl compounds on reaction with trimethylsilyl iodide (in situ prepared from TMSCI/NaI) led to the formation of diazepine imines in good yields under mild conditions. This methodology has been applied to the parent unsubstituted pyrrolobenzodiazepine, the natural product DC-81 and its dimers. (C) 2000 Elsevier Science Ltd.

A new methodology for the reductive cyclization of ω-azido carbonyl compounds mediated by tetrathiomolybdate: Application to an efficient synthesis of pyrrolo[2,1-c][1,4]benzodiazepines

The ω-azido carbonyl compounds on treatment with tetrathiomolybdate, 1 led to the formation of 5, 6 and 7 membered cyclic imines in very good yields under mild conditions. This method is applied successfully to a new efficient synthesis of 1,4-benzodiazap

Novel biocatalytic reduction of aryl azides: Chemoenzymatic synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics

The chemoselective reduction of aryl azides to aryl amines, and the synthesis of the imine-containing pyrrolo[2,1-c][1-4]benzodiazepine DNA-binding antitumour antibiotics by selective biocatalytic reductive cyclization of azido aldehydes, has been achieved by employing baker's yeast.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepine antibiotics via azido reductive cyclization with HMDST

A new facile synthesis of pyrrolo[2,1-c][1,4]benzodiazepine (PBD) ring system has been achieved by reductive cyclization of the azide employing hexamethyldisilathiane (HMDST). The parent unsubstituted PBD and the natural product DC-81 have also been prepared in good overall yields.

Facile Synthesis of 1,4-Benzodiazepin-5-one Derivatives via Intramolecular Aza-Wittig Reaction. Application to an Efficient Synthesis of O-Benzyl DC-81

The tandem Staudinger/aza-Wittig reaction of N-(o-azidobenzoyl)-α-amino acid esters gave the corresponding 1,4-benzodiazepin-5-one derivatives in moderate to good yields.This method was applied successfully to a new efficient synthesis of BzlDC-81.

Synthesis of pyrrolo[2,1-c][1,4]benzodiazepines via an intramolecular aza-Wittig reaction. Synthesis of the antibiotic DC-81

A new and efficient synthesis of the pyrrolo[2,1-c][1,4]benzodiazepine ring system has been carried out using, as a key step, an intramolecular aza-Wittig reaction of the appropriately substituted N-(2-azidobenzoyl)pyrrolidine-2-carboxaldehydes. The paren