2-O-(5-broMo-4-chloroindol-3-yl)sialic acid

Base Information

• Chemical Name: 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid
• CAS No.: 153248-52-3
• Molecular Formula: C19H22BrClN2O9
• Molecular Weight: 537.74
• Mol file: 153248-52-3.mol

Synonyms:2-O-(5-broMo-4-chloroindol-3-yl)sialic acid;5-bromo-4-chloro-indol-3-yl-(5-acetamido-3,5-dideoxy-alfa-D-glycero-D-galacto-2-nonulopyranosylonic acid);a-Neuraminic acid, N-acetyl-2-O-(5-bromo-4-chloro-1H-indol-3-yl)-;

Chemical Property of 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid

Chemical Property:

• PSA: 181.57000
• LogP: 0.50300

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid

There total 19 articles about 2-O-(5-broMo-4-chloroindol-3-yl)sialic acid 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: 88.0%

(5-bromo-4-chloro-indol-3-yl)-(methyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate) (1447125-47-4) → 5-bromo-4-chloro-indol-3-yl-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid) (153248-52-3)

Guidance literature:

(5-bromo-4-chloro-indol-3-yl)-(methyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate); With sodium hydroxide; In water; at 20 ℃; for 2h;

DOI:10.1021/ol401710a

Reference yield: 46.5%

C23H28BrClN2O11 → 5-bromo-4-chloro-indol-3-yl-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid) (153248-52-3)

Guidance literature:

With water; sodium hydroxide; at 45 ℃; for 16h;

Reference yield:

1-acetyl-5-bromo-4-chloroindolin-3-one (116270-39-4) + methyl 4,7,8,9-tetra-O-acetyl-2-chloro-5-(N,N-diacetylamino)-2,3,5-trideoxy-β-D-glycero-D-galacto-non-2-ulo-pyranosonate (1227673-26-8) + tetra(n-butyl)ammonium hydrogensulfate (32503-27-8) → 5-bromo-4-chloro-indol-3-yl-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid) (153248-52-3) + C19H21BrClN2O9(1-)*C16H36N(1+)

Guidance literature:

1-acetyl-5-bromo-4-chloroindolin-3-one; methyl 4,7,8,9-tetra-O-acetyl-2-chloro-5-(N,N-diacetylamino)-2,3,5-trideoxy-β-D-glycero-D-galacto-non-2-ulo-pyranosonate; tetra(n-butyl)ammonium hydrogensulfate; With sodium carbonate; In water; ethyl acetate; at 20 ℃; for 21h;

With triethylamine; In methanol; water; for 17h; Overall yield = 38 %; Overall yield = 87.8 mg;

DOI:10.1007/s11172-017-1999-x

upstream raw materials:

C₁₃H₉BrClNO₅

C₁₅H₁₅BrClNO₄

5-bromo-4-chloroindoxylic acid allyl ester

5-bromo-4-chloro-indox-3-ylic acid allyl ester-(methyl-5-acetamido-4,7,8,9-tetra-Oacetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)