(2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate

Base Information

• Chemical Name: (2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate
• CAS No.: 176590-77-5
• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.337
• DSSTox Substance ID: DTXSID10365511
• Wikidata: Q82150244
• Mol file: 176590-77-5.mol

Synonyms:(2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate;176590-77-5;[(2R,3R)-4-benzoyloxy-2,3-dihydroxybutyl] benzoate;SCHEMBL1862116;DTXSID10365511;AKOS022173379;CS-0448488;A812194;[(2R,3R)-4-benzoyloxy-2,3-dihydroxy-butyl] benzoate

Chemical Property of (2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate

Chemical Property:

• Vapor Pressure: 6.92E-12mmHg at 25°C
• Refractive Index: 1.591
• Boiling Point: 525.9& #176;Cat760mmHg
• Flash Point: 190.2 °C
• PSA: 93.06000
• Density: 1.295 g/cm³
• LogP: 1.42220
• Storage Temp.: 2-8°C
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 330.11033829
• Heavy Atom Count: 24
• Complexity: 360

Purity/Quality:

99% ^*data from raw suppliers

(2R,3R)-2,3-Dihydroxybutane-1,4-diyldibenzoate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)OCC(C(COC(=O)C2=CC=CC=C2)O)O
• Isomeric SMILES: C1=CC=C(C=C1)C(=O)OC[C@H]([C@@H](COC(=O)C2=CC=CC=C2)O)O

Technology Process of (2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate

There total 12 articles about (2R,3R)-2,3-Dihydroxybutane-1,4-diyl dibenzoate 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: 97.0%

1,4-dibenzoyloxy-2-butene (64991-07-7) → 1,4-dibenzoylerythritol (201294-49-7,176590-77-5,929558-08-7)

Guidance literature:

With 4-methylmorpholine N-oxide; potassium osmate(VI); In water; acetone; at 20 ℃; for 5h;

Reference yield: 95.0%

cis-1,4-dibenzoyloxybut-2-ene (55759-12-1) → anti-2,3-dihydroxybutane-1,4-diyl dibenzoate (74793-33-2,176590-77-5,929558-08-7)

Guidance literature:

With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In acetone; at 20 ℃;

DOI:10.1055/s-0030-1258560

Reference yield:

D-threitol (2418-52-2,10030-58-7,188346-77-2,149-32-6) + benzoyl chloride (98-88-4) → (2R,3R)-2,3-dihydroxybutane-1,4-diyl dibenzoate (176590-77-5,929558-08-7)

Guidance literature:

In 1-methyl-pyrrolidin-2-one; at 20 - 50 ℃; for 2h;

upstream raw materials:

meso-erythritol

benzoyl chloride

benzoic acid

meso-1,2,3,4-diepoxybutane

Downstream raw materials:

benzoyloxy-acetaldehyde-(2,4-dinitro-phenylhydrazone)

2-benzoyloxyacetaldehyde

Refernces

• 1、 -. "OMEGA-3 FATTY ACID PRODRUG COMPOUNDS AND USES THEREOF". Page/Page column 23. . Retrieved 2016/09/22.
• 2、 Dornan, Peter K.,Wickens, Zachary K.,Grubbs, Robert H.. "Tandem Z-Selective Cross-Metathesis/Dihydroxylation: Synthesis of anti-1,2-Diols". supporting information. p. 7134 - 7138. Retrieved 2015/06/16.