2,3,4-Tri-O-acetyl-D-arabinopyranosyl bromide

Base Information

• Chemical Name: 2,3,4-Tri-O-acetyl-D-arabinopyranosyl bromide
• CAS No.: 113889-50-2
• Molecular Formula: C11H15BrO7
• Molecular Weight: 339.14
• DSSTox Substance ID: DTXSID00393101
• Mol file: 113889-50-2.mol

Synonyms:2,3,4-Tri-O-acetyl-D-arabinopyranosyl bromide;113889-50-2;(4,5-diacetyloxy-6-bromooxan-3-yl) acetate;beta-L-Arabinopyranosyl bromide, 2,3,4-triacetate;Tri-O-acetyl-beta-D-arabinosylbromide;14227-90-8;2,3,4-O-triacetyl-A-D-bromo xylose;TRI-O-ACETYL-BETA-L-ARABINOSYLBROMIDE;SCHEMBL18961117;DTXSID00393101;AKOS025294106;FT-0634636;FT-0771854

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

Chemical Property:

• 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:

98%Min ^*data from raw suppliers

2-3-4-Tri-O-acetyl-D-arabinopyranosylbromide-Stabilisedwith2%CaCO3 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1COC(C(C1OC(=O)C)OC(=O)C)Br

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

There total 7 articles about 2,3,4-Tri-O-acetyl-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:

(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (108646-05-5) → (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (113889-50-2)

Guidance literature:

With hydrogen bromide; In water; acetic acid; at 0 ℃; for 1h;

DOI:10.1021/jo020309w

Reference yield:

D-arabinopyranose (28697-53-2) → (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (113889-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 16 h / 0 °C

2: HBr / H₂O; acetic acid / 1 h / 0 °C

With pyridine; hydrogen bromide; In water; acetic acid;

DOI:10.1021/jo020309w

Reference yield:

2,3,4-tri-O-acetyl-D-arabinopyranose (10369-25-2,70135-47-6,86032-22-6,86032-23-7,101857-06-1,106820-14-8,120019-52-5) → (3S,4R,5R)-2-bromotetrahydro-2H-pyran-3,4,5-triyl triacetate (113889-50-2)

Guidance literature:

With water; bromine;

DOI:10.1039/a910166g

upstream raw materials:

2,3,4-tri-O-acetyl-D-arabinopyranose

(3S,4R,5R)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

D-arabinopyranose

D-Arabinose

Downstream raw materials:

3,4-di-O-acetyl-D-arabinal

(3S,4aR,5S,8R,8aS)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-ethano-1H-2-benzopyran-4(3H)-one

(3S,4aS,5R,8S,8aR)-3-benzyloxy-4a,5,8,8a-tetrahydro-5,8-methano-1H-2-benzopyran-4(3H)-one

Refernces

• 1、 Nemcsok, Tamás,Rapi, Zsolt,Bagi, Péter,Keglevich, Gy?rgy,Bakó, Péter. "Synthesis of xylal- and arabinal-based crown ethers and their application as asymmetric phase transfer catalysts". . p. 107 - 119. Retrieved 2019/11/16.
• 2、 Perali, Ramu Sridhar,Bandi, Anjaneyulu. "Stereoselective total synthesis of all the stereoisomers of (+)- and (?)-febrifugine and halofuginone". . . Retrieved 2020/07/04.