193887-70-6

Upstream product

• 136672-34-9 1-azido-2-chloro-4-methylbenzene 
• 615-65-6 2-chloro-4-methyl-benzenamine 

Downstream Products

• 193887-71-7 (2R,3R,4S,5R,6S)-2-(4-Azido-3-chloro-benzyloxymethyl)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran 
• 193887-72-8 (2R,3R,4S,5R,6S)-3-(4-Azido-3-chloro-benzyloxy)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran 
• 210834-00-7 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside 
• 210834-04-1 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside 
• 1235973-11-1 allyl 3-O-(4-azido-3-chlorobenzyl)-4,6-O-benzylidene-α-D-mannopyranoside 
• 210834-06-3 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzoyl-1-thio-β-D-glucopyranoside 
• 210834-05-2 phenyl 6-O-(4-azido-3-chlorobenzyl)-1-thio-β-D-glucopyranoside 
• 617698-90-5 3-O-(4-azido-3-chlorobenzyl)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 617698-87-0 phenyl (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-1-thio-β-D-glucopyranoside 
• 617698-88-1 4-{[(3-carboxypropanoyl)oxy]methyl}benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside 
• 617698-95-0 phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4-O-benzyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside 
• 617698-93-8 4-(hydroxymethyl)benzyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-4,6-di-O-benzyl-β-D-glucopyranoside 
• 617698-94-9 phenyl 3-O-(4-azido-3-chlorobenzyl)-2-O-benzoyl-6-O-(triphenylmethyl)-1-thio-β-D-glucopyranoside 
• 617698-91-6 phenyl 3-O-(4-azido-3-chlorobenzyl)-2,4,6-tri-O-benzoyl-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

Revisiting the bromination of c-h bonds with molecular bromine by using a photo-microflow system

The photobromination of C-H bonds by using molecular bromine was reinvestigated under microfluidic conditions. The continuous-flow method suppressed the production of dibrominated compounds and effectively produced the desired monobrominated products with high selectivity. Rapid bromination of benzylic substrates containing a photoaffinity azide group was achieved without any decomposition. Go with the (micro)flow: Photobromination of C-H bonds by using molecular bromine under microfluidic conditions has been investigated (see scheme). The continuous-flow method suppressed the production of dibrominated compounds and effectively produced the desired monobrominated compounds with high selectivity. Rapid bromination of benzylic substrates containing a photoaffinity azide group was achieved without any decomposition.

Azidohalogenobenzyl derivatives, sugar compounds and protection of hydroxy groups

Azidohalogenobenzyl derivatives of the formula (I) STR1 wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.

4-Azido-3-chlorobenzyl Ether, New Protection for Hydroxy Functions

The 4-azido-3-chlorobenzyl (Cl-Azb) group was readily introduced to hydroxy functions by the use of a crystalline reagent, 4-azido-3-chlorobenzyl bromide, which was prepared from commercially available 2-chloro-4-methylaniline in two steps. Cl-Azb ethers have improved acid stability as compared to the corresponding parent 4-azidobenzyl (Azb) ether. Cl-Azb ethers were stable to direct 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) oxidation, but were cleaved smoothly by DDQ oxidation after conversion to the corresponding iminophosphorane derivative.