2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl bromide

Base Information

• Chemical Name: 2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl bromide
• CAS No.: 14227-90-8
• Molecular Formula: C11H15BrO7
• Molecular Weight: 339.14
• Hs Code.: 2932999099
• European Community (EC) Number: 622-432-4
• DSSTox Substance ID: DTXSID30931398
• Nikkaji Number: J83.273A
• Wikidata: Q76416599
• Mol file: 14227-90-8.mol

Synonyms:3068-29-9;2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl bromide;(2S,3S,4R,5R)-2-Bromotetrahydro-2H-pyran-3,4,5-triyl triacetate;14227-90-8;Tri-O-acetyl-beta-D-arabinosylbromide;.beta.-L-Arabinopyranosyl bromide, triacetate;starbld0014417;SCHEMBL5348565;DTXSID30931398;AVNRQUICFRHQDY-CHWFTXMASA-N;MFCD09864634;AKOS015912757;Tri-O-acetyl- beta -D-arabinosylbromide;2,3,4-Tri-O-acetylpentopyranosyl bromide;I(2)-D-Arabinopyranosyl bromide, triacetate;Tri-O-acetyl-beta-D-arabinosylbromide, 95%;.beta.-D-Arabinopyranosyl bromide, triacetate;Arabinopyranosyl bromide, triacetate, .beta.-D-;J-018053;2-O,3-O,4-O-Triacetyl-beta-D-arabinopyranosyl bromide

Chemical Property of 2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl bromide

Chemical Property:

• Melting Point: 136-140 °C(lit.)
• PSA: 88.13000
• LogP: 0.53270
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 338.00012
• Heavy Atom Count: 19
• Complexity: 370

Purity/Quality:

99% ^*data from raw suppliers

2,3,4-TRI-O-ACETYL-BETA-L-ARABINOPYRANOSYL BROMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)Br
• Isomeric SMILES: CC(=O)O[C@@H]1CO[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)Br

Technology Process of 2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl bromide

There total 14 articles about 2,3,4-tri-O-acetyl-beta-D-arabinopyranosyl 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: 79.0%

1,2,3,4-tetra-O-acetyl-β-L-arabinopyranose (4258-00-8) → 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (14227-90-8)

Guidance literature:

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

DOI:10.1021/acs.orglett.7b02760

Reference yield: 78.0%

1,2,3,4-tetra-O-acetyl-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3) → 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (14227-90-8)

Guidance literature:

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

DOI:10.1016/j.carres.2008.01.046

Reference yield: 72.0%

L-arabinose (5328-37-0) + acetic anhydride (108-24-7) → 2,3,4-tri-O-acetyl-α-L-arabinopyranosyl bromide (14227-90-8)

Guidance literature:

With hydrogen bromide; In acetic acid; at 20 ℃;

DOI:10.1055/s-0035-1562617

upstream raw materials:

Acetyl bromide

L-arabinose

acetic anhydride

1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose

Downstream raw materials:

paeonovicianoside hexaacetate

2-α-L-arabinopyranosyloxy-benzoic acid methylamide

1-(4-nitrophenyl)-α-L-arabinopyranoside

2-α-L-arabinopyranosyloxy-benzoic acid dimethylamide

Refernces

• 1、 Xu, Kun-Lun,Yu, Lan. "Neuroprotective activity of different monosaccharide-modified gastrodin analogs". . p. 1263 - 1269. Retrieved 2020/01/21.
• 2、 Dada, Lucas,Manzano, Verónica E.,Varela, Oscar. "Synthesis of enantiomerically pure enones (2-benzyloxypyran-3-ones)derived from pentoses". . p. 31 - 40. Retrieved 2019/05/24.