2,3,4-Tri-O-benzoylfucopyranosyl bromide

Base Information

• Chemical Name: 2,3,4-Tri-O-benzoylfucopyranosyl bromide
• CAS No.: 131897-73-9
• Molecular Formula: C27H23 Br O7
• Molecular Weight: 539.379
• DSSTox Substance ID: DTXSID20157242
• Nikkaji Number: J2.448.445I
• Wikidata: Q83025392
• Mol file: 131897-73-9.mol

Synonyms:2,3,4-tri-O-benozyl-alpha-fucopyranosyl bromide;2,3,4-tri-O-benzoylfucopyranosyl bromide;tri-Bz-Fuc-Br

Chemical Property of 2,3,4-Tri-O-benzoylfucopyranosyl bromide

Chemical Property:

• Vapor Pressure: 2.18E-15mmHg at 25°C
• Melting Point: 169 - 171 °C
• Boiling Point: 621.9°C at 760 mmHg
• Flash Point: 329.9°C
• PSA: 88.13000
• Density: 1.46g/cm³
• LogP: 4.80290
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 9
• Exact Mass: 538.06272
• Heavy Atom Count: 35
• Complexity: 725

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)Br)OC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)Br)OC(=O)C2=CC=CC=C2)OC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4

Technology Process of 2,3,4-Tri-O-benzoylfucopyranosyl bromide

There total 21 articles about 2,3,4-Tri-O-benzoylfucopyranosyl 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: 96.0%

(3S,4R,5R,6S)-6-methyltetrahydro-2H-pyran-2,3,4,5-tetrayl tetrabenzoate (140223-15-0) → 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl bromide (131897-73-9)

Guidance literature:

With water; phosphorus tribromide; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.carres.2008.01.046

Reference yield: 94.4%

methyl 2,3,4-tri-O-benzoyl-1-thio-α-L-rhamnopyranoside (115678-19-8) → 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (14218-08-7,41881-44-1,53297-33-9,60820-93-1,61198-82-1,67986-91-8,73068-86-7,131897-72-8,131897-73-9)

Guidance literature:

With bromine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1021/jo00252a030

Reference yield: 92.0%

1,2,3,4-tetra-O-benzoyl-α-L-fucopyranoside (135266-93-2) → 2,3,4-tri-O-benzoyl-α-L-fucopyranosyl bromide (131897-73-9)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/acs.orglett.7b02760

upstream raw materials:

1,2,3,4-tetra-O-benzoyl-6-desoxy-α-L-mannopyranose

L-rhamnose monohydrate

benzoyl chloride

L-Rhamnose

Downstream raw materials:

O²,O³,O⁴-Tribenzoyl-L-rhamnose

3,4-di-O-benzoyl-1,2-O-(alpha-methoxybenzylidene)-beta-L-rhamnopyranose

methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-β-D-glucopyranoside

methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

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