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for oligosaccharide synthesis
4-Azido-3-chlorobenzyl Bromide (Cl-Azb)

Many attempts have been made to devise efficient methods to synthesize oligosaccharides. However, these chains have many hydroxyl groups that make position-specific branch extension difficult. Efforts until now focused on designing and synthesizing various means of protecting the hydroxyl group of the acceptor.
Cl-Azb is a protective reagent for hydroxyl groups on saccharides that features improved acid stability compared to the conventional 4-Azidobenzyl (Azb) group.
Like Azb, de-protection can be achieved rapidly by reacting with triphenyl phosphine (PPh3) for conversion into a corresponding iminophosphorane derivative, which is then oxidized with 2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ).
Unlike Azb, which is directly cleaved by DDQ oxidation, Cl-Azb exhibits superior acid stability. In addition, selective de-protection of p-Methoxybenzyl (MPM) groups with direct DDQ oxidation is also possible when MPM groups are present(1), and this in turn enables position-specific chain extension.


INDEX

  1. Chemical structure

  2. Reaction example(1)

  3. Reference

  4. Product list

  5. Related products




1. Chemical structure



2. Reaction example (1)



3. Reference
(1) Egasa , K. , Fukase , K. and Kusumoto S.: 4-Azido-3-chlorobenzyl Ether, New Protection for Hydroxy Functions", SYNLETT, 6, 675 (1997).



4. Product list
Product Name Grade Pkg. size Wako Catalog No.
4-Azido-3-chlorobenzyl Bromide for Sugar Synthesis 1 g 013-16961
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5. Related product
Product Name Grade Pkg. size Wako Catalog No.
2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) Practical Grade 1 g 049-06331
10 g 045-06333
Triphenyl Phosphine (PPh3) Wako Special Grade 25 g 202-03062
500 g 206-03065
p-Methoxybenzyl Chloride - 25 g 139-05462
N,N-Dimethylformamide, Super Dehydrated
(water content: ≤ 10 ppm)
for Organic Synthesis 100 mL 043-32361
500 mL 045-32365
3 L 049-32363
Ethyl Acetate , Super Dehydrated
(water content: ≤ 10 ppm)
for Organic Synthesis 100 mL 055-08173
500 mL 057-08175
3 L 051-08171
Tetrahydrofuran , Super Dehydrated, with Stabilizer
(water content: ≤ 10 ppm)
for Organic Synthesis 100 mL 205-17901
500 mL 205-17905
3 L 209-17904
· Each Super Dehydrated Solvent has its expiry date, respectively.
· Super Dehydrated Solvents other than the above are also available.
· Deoxygenated Solvents guaranteed for dissolved oxygen content being not more than 1 ppm and
water content being not more than 0.001% (10 ppm) and Dehydrated Solvents guaranteed for water content are also available.


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Home > Products > Chemicas > 4-Azido-3-chlorobenzyl Bromide (Cl-Azb)