5-Bromo-4-chloro-3-indolyl beta-D-cellobioside

Base Information

• Chemical Name: 5-Bromo-4-chloro-3-indolyl beta-D-cellobioside
• CAS No.: 177966-52-8
• Molecular Formula: C₂₀H₂₅BrClNO₁₁
• Molecular Weight: 570.776
• Hs Code.: 29389090
• European Community (EC) Number: 634-018-0
• Nikkaji Number: J3.092.932B
• Wikidata: Q76422600
• Mol file: 177966-52-8.mol

Synonyms:177966-52-8;5-BROMO-4-CHLORO-3-INDOLYL BETA-D-CELLOBIOSIDE;5-Bromo-4-chloro-3-indoxyl-beta-D-cellobioside;5-Bromo-4-chloro-3-indolyl b-D-cellobioside;5-Bromo-4-chloro-3-indolyl |A-D-cellobioside;(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(5-bromo-4-chloro-1H-indol-3-yl)oxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-6-((5-bromo-4-chloro-1H-indol-3-yl)oxy)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;X-Cellobioside;X-beta-D-cellobioside;MFCD00798387;AKOS015919300;HY-W337201;TS-09164;CS-0448554;B-7110;5-Bromo-4-chloro-3-indolyl beta -D-cellobioside;B-D-GLUCOPYRANOSIDE,5-BROMO-4-CHLORO-1H-INDOL-3-YL 4-O-B-D-GLUCOPYRANOSYL-;beta-D-Glucopyranoside, 5-bromo-4-chloro-1H-indol-3-yl 4-O-beta-D-glucopyranosyl-;2-[6-[(5-BROMO-4-CHLORO-1H-INDOL-3-YL)OXY]-4,5-DIHYDROXY-2-(HYDROXYMETHYL)OXAN-3-YL]OXY-6-(HYDROXYMETHYL)OXANE-3,4,5-TRIOL

Chemical Property of 5-Bromo-4-chloro-3-indolyl beta-D-cellobioside

Chemical Property:

• PSA: 194.32000
• Density: 1.91±0.1 g/cm3 (20 oC 760 Torr), Calc.*
• LogP: -1.41330
• Storage Temp.: −20°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 6
• Exact Mass: 569.02995
• Heavy Atom Count: 34
• Complexity: 684

Purity/Quality:

98% ^*data from raw suppliers

5-Bromo-4-chloro-3-indolyl b-D-cellobioside ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C2=C1NC=C2OC3C(C(C(C(O3)CO)OC4C(C(C(C(O4)CO)O)O)O)O)O)Cl)Br
• Isomeric SMILES: C1=CC(=C(C2=C1NC=C2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O)Cl)Br

Technology Process of 5-Bromo-4-chloro-3-indolyl beta-D-cellobioside

There total 14 articles about 5-Bromo-4-chloro-3-indolyl beta-D-cellobioside 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: 75.0%

(N-acetyl-5-bromo-4-chloroindol-3-yl) (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4))-2,3,6-tri-O-acetyl-β-D-glucopyranoside (1607828-62-5) → (5-bromo-4-chloroindol-3-yl) (β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside (1607828-63-6,177966-52-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

DOI:10.1002/ejoc.201301198

Reference yield:

N-acetyl-5-bromo-6-chloroanthranilic acid (125328-77-0) → (5-bromo-4-chloroindol-3-yl) (β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside (1607828-63-6,177966-52-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: sodium hydroxide; water / 4 h / Reflux

2.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

3.2: Inert atmosphere

4.1: sodium methylate / 2 h / 40 - 45 °C / Inert atmosphere

5.1: sodium methylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

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

7.1: sodium methylate / methanol / 20 °C

8.1: sodium hydroxide / water / 40 - 45 °C

9.1: potassium carbonate; silver(I) acetate / 1 h / 110 °C

10.1: sodium methylate / methanol / 20 °C

With pyridine; water; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 5.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

Reference yield:

2-amino-5-bromo-6-chlorobenzoic acid (3030-19-1) → (5-bromo-4-chloroindol-3-yl) (β-D-galactopyranosyl)-(1→4)-β-D-glucopyranoside (1607828-63-6,177966-52-8)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine / dichloromethane; acetonitrile / 3.5 h / 45 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.75 h / Inert atmosphere; Cooling with ice

2.2: Inert atmosphere

3.1: sodium methylate / 2 h / 40 - 45 °C / Inert atmosphere

4.1: sodium methylate / diethyl ether / 2 h / 40 - 45 °C / Inert atmosphere

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

6.1: sodium methylate / methanol / 20 °C

7.1: sodium hydroxide / water / 40 - 45 °C

8.1: potassium carbonate; silver(I) acetate / 1 h / 110 °C

9.1: sodium methylate / methanol / 20 °C

With pyridine; sodium methylate; silver(I) acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; sodium hydroxide; In methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: |Dieckmann Condensation;

DOI:10.1002/ejoc.201301198

upstream raw materials:

N-acetyl-5-bromo-6-chloroanthranilic acid

2-amino-5-bromo-6-chlorobenzoic acid

5-bromo-6-chloro-isatoic anhydride

5-bromo-6-chloro-N-[(methoxycarbonyl)methyl]-isatoic anhydride

Refernces