2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

Base Information

• Chemical Name: 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
• CAS No.: 572-09-8
• Molecular Formula: C14H19BrO9
• Molecular Weight: 411.203
• Hs Code.: 29329985
• European Community (EC) Number: 209-339-0
• UNII: ETH4010665
• DSSTox Substance ID: DTXSID001031860
• Nikkaji Number: J6.538B
• Wikidata: Q27277359
• Mol file: 572-09-8.mol

Synonyms:572-09-8;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide;Acetobromglucose;acetobromoglucose;Acetobromo-alpha-D-glucose;2,3,4,6-Tetra-O-acetyl-|A-D-glucopyranosyl bromide;C14H19BrO9;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate;UNII-ETH4010665;EINECS 209-339-0;ETH4010665;[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-bromooxan-2-yl]methyl acetate;a-acetobromglucose;2,3,4,6-tetra-o-acetyl--d-glucopyranosyl bromide;Bromo 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranoside;MFCD00063254;Acetobromo glucose;C14-H19-Br-O9;d-acetobromoglucose;alpha-acetobromoglucose;.alpha.-D-Glucopyranosyl bromide, tetraacetate;2,3,4,6-tetra-o-acetyl-alpha-d-glucopyranosyl;ACETOBROMGLUCOSE [MI];Acetobromo- alpha -D-glucose;SCHEMBL989356;2,3,4,6-O-Tetraacetyl-alpha-D-glucopyranosyl bromide;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosylbromide;DTXSID001031860;AMY24725;ACETOBROMO-.ALPHA.-D-GLUCOSE;NSC783071;AKOS015896857;NSC-783071;(2R,3R,4S,5R,6R)-2-(Acetoxymethyl)-6-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide, stab. with 2% calcium carbonate;AS-16072;alpha-D-Glucopyranosyl bromide, tetraacetate;Acetobromo-alpha-D-glucose, >=95% (TLC);I+/--D-Glucopyranosyl bromide, tetraacetate;T1961;EN300-69301;10.14272/CYAYKKUWALRRPA-RGDJUOJXSA-N;F14901;A831344;doi:10.14272/CYAYKKUWALRRPA-RGDJUOJXSA-N;2,3,4,6-tetra-O-acetyl-alpha-glucopyranosyl bromide;2,3,4,6-Tetra-O-acetylalpha-D-glucopyranosyl bromide;alpha-D-Glucopyranosyl bromide 2,3,4,6-tetraacetate;Q27277359;2,3,4,6-tetra-O-acetyl-alpha-D-glycopyranosyl bromide;2.2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide;2,3,4,6-TETRAACETYL-.ALPHA.-D-GLUCOPYRANOSYL BROMIDE;2,3,4,6-tetra-O-Acetyl-|A inverted exclamation mark-D-glucopyranosyl;[(3R,5R,6R)-3,4,5-triacetoxy-6-bromo-tetrahydropyran-2-yl]methyl acetate;2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl Bromide

Chemical Property of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

Chemical Property:

• Appearance/Colour: white fluffy solid
• Melting Point: 86-89 °C
• Refractive Index: 1.541
• Boiling Point: 412 °C at 760 mmHg
• Flash Point: 203 °C
• PSA: 114.43000
• Density: 1.49 g/cm³
• LogP: 0.46440
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: decomposes
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 9
• Exact Mass: 410.02124
• Heavy Atom Count: 24
• Complexity: 507

Purity/Quality:

99% ^*data from raw suppliers

Bromo 2,3,4,6-Tetra-O-acetyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: An Intermediate in synthesis of ∫-glucosides Acetobromo-α-D-glucose acts as an intermediate in the preparation of beta-glucosides. It is also used as a possible poly(ethylene terephthalate) surface modification reagent to enhance its blood compatibility.

Technology Process of 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

There total 98 articles about 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide 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: 100.0%

β-D-glucose pentaacetate (604-69-3) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Guidance literature:

With hydrogen bromide; In dichloromethane; Ambient temperature;

DOI:10.1016/S0040-4020(96)00349-3

Reference yield: 100.0%

α-D-glucopyranose peracetylate (604-68-2) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Guidance literature:

With hydrogen bromide; acetic acid;

DOI:10.3390/molecules24050949

Reference yield: 97.0%

p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Guidance literature:

With Acetyl bromide; zinc dibromide; In dichloromethane; at 22 ℃; for 24h;

DOI:10.1016/S0008-6215(96)90118-4

upstream raw materials:

D-glucose

sodium chloride * 2 d-glucose * H₂O

acetic anhydride

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Downstream raw materials:

2-phenyl-4H-chromen-4-one-3-O-2,3,4,6-O-tetraacetyl-β-d-glucopyranoside

phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside]

benzyl-[O²,O³-dibenzyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside]

glucofranguline A

Refernces

Concise synthesis of 5-methoxy-6-hydroxy-2-methylchromone-7-O- and 5-hydroxy-2-methylchromone-7-O-rutinosides. Investigation of their cytotoxic activities against several human tumor cell lines

10.1021/jo102325s

The research aimed to develop a concise synthetic strategy for the production of two novel 2-methylchromone-7-O-rutinosides, which are flavonoid glycosides with potential cytotoxic activities against human tumor cell lines. The study was driven by the bioactivities of these compounds, particularly their potential as antitumor agents with low side effects on normal cells. The synthesis process involved the use of various chemicals, including Visnagin, chromic acid, hydrogen peroxide, 2,3,4,6-tetra-O-acetyl-R-D-glucosyl bromide, Bu4NBr, K2CO3, 1,4-diazabicyclo[2.2.2]octane (DABCO), trityl chloride, bismuth trichloride, and trichloroacetimidate derivatives. The researchers successfully synthesized the target compounds and evaluated their in vitro cytotoxicity against several human cancer cell lines.

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