5-BROMO-4-CHLORO-3-INDOXYL-BETA-L-FUCOPYRANOSIDE

Base Information

• Chemical Name: 5-BROMO-4-CHLORO-3-INDOXYL-BETA-L-FUCOPYRANOSIDE
• CAS No.: 125328-84-9
• Molecular Formula: C₁₄H₁₅BrClNO₅
• Molecular Weight: 392.634
• Hs Code.: 29400090
• Mol file: 125328-84-9.mol

Synonyms:5-Bromo-4-chloro-3-indolyl |A-L-fucopyranoside;W0443;

Chemical Property of 5-BROMO-4-CHLORO-3-INDOXYL-BETA-L-FUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 8.63E-16mmHg at 25°C
• Boiling Point: 611.1oC at 760 mmHg
• Flash Point: 323.4oC
• PSA: 94.94000
• Density: 1.796g/cm3
• LogP: 1.79010
• Storage Temp.: −20°C

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-4-chloro-3-indolyl b-L-fucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-BROMO-4-CHLORO-3-INDOXYL-BETA-L-FUCOPYRANOSIDE

There total 12 articles about 5-BROMO-4-CHLORO-3-INDOXYL-BETA-L-FUCOPYRANOSIDE 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: 99.0%

(N-acetyl-5-bromo-4-chloro-indol-3-yl)-2,3,4-tri-O-acetyl-β-L-fucopyranoside (1447125-37-2) → (5-Bromo-4-chloro-indol-3-yl)-β-L-fucopyranoside (125328-84-9,17016-46-5,171869-92-4)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 1h;

DOI:10.1021/ol401710a

Reference yield:

C13H9BrClNO5 (1447125-22-5) → (5-Bromo-4-chloro-indol-3-yl)-β-L-fucopyranoside (125328-84-9,17016-46-5,171869-92-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / paraffin oil / 6.5 h / 20 °C

2.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

3.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C

4.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Darkness

4.2: 0.3 h / 90 - 100 °C / Inert atmosphere; Darkness

5.1: sodium methylate; methanol / 1 h / 20 °C

With morpholine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; paraffin oil; 2.1: |Dieckmann Condensation;

DOI:10.1021/ol401710a

Reference yield:

C15H15BrClNO4 (1447125-25-8) → (5-Bromo-4-chloro-indol-3-yl)-β-L-fucopyranoside (125328-84-9,17016-46-5,171869-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium tert-butylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

2.1: potassium carbonate; tetra(n-butyl)ammonium hydrogensulfate / water; dichloromethane / 5 h / 20 °C

3.1: morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Darkness

3.2: 0.3 h / 90 - 100 °C / Inert atmosphere; Darkness

4.1: sodium methylate; methanol / 1 h / 20 °C

With morpholine; methanol; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium tert-butylate; sodium methylate; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; 1.1: |Dieckmann Condensation;

DOI:10.1021/ol401710a

upstream raw materials:

C₁₃H₉BrClNO₅

C₁₅H₁₅BrClNO₄

5-bromo-4-chloroindoxylic acid allyl ester

(5-bromo-4-chloro-indox-3-ylic acid allyl ester)-2,3,4-tri-O-acetyl-β-L-fucopyranoside

Refernces