(-)-1,4-ANHYDRO-L-THREITOL

Base Information

• Chemical Name: (-)-1,4-ANHYDRO-L-THREITOL
• CAS No.: 4358-64-9
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 2932190090
• European Community (EC) Number: 224-433-1
• DSSTox Substance ID: DTXSID401318325
• Nikkaji Number: J205.737I
• Mol file: 4358-64-9.mol

Synonyms:3,4-Furandiol,tetrahydro-, cis-;(3S,4R)-Tetrahydrofuran-3,4-diol;cis-3,4-Dihydroxyoxolane;cis-3,4-Dihydroxytetrahydrofuran;cis-Oxolane-3,4-diol;cis-Tetrahydrofuran-3,4-diol;

Chemical Property of (-)-1,4-ANHYDRO-L-THREITOL

Chemical Property:

• Vapor Pressure: 0.0216mmHg at 25°C
• Melting Point: 173-174 °C
• Refractive Index: n20/D 1.477(lit.)
• Boiling Point: 221.8 °C at 760 mmHg
• PKA: 13.66±0.40(Predicted)
• Flash Point: 104 °C
• PSA: 49.69000
• Density: 1.411 g/cm³
• LogP: -1.26160
• Storage Temp.: 2-8°C
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 56

Purity/Quality:

98% ^*data from raw suppliers

1,4-Anhydroerythrito ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(CO1)O)O
• Isomeric SMILES: C1[C@H]([C@H](CO1)O)O
• Uses: 1,4-Anhydroerythritol is a tetrahydrofuran derivative used as a heterocyclic building block in epoxy resins and other polymers. 1,4-Anhydroerythritol is also used in the preparation of nucleotide anal ogs as potential antiviral and anticancer agents. 1,4-Anhydroerythritol was employed in a key step in the synthesis of glucopyranoside-based analogs of adenophostin A lacking the adenine component.

Technology Process of (-)-1,4-ANHYDRO-L-THREITOL

There total 20 articles about (-)-1,4-ANHYDRO-L-THREITOL 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: 95.0%

meso-erythritol (909878-64-4,10030-58-7,188346-77-2,149-32-6) → cis-1,4-anhydroerythritol (4358-64-9)

Guidance literature:

With Dowex 50 W 4; at 150 ℃;

DOI:10.1016/S0957-4166(00)80064-6

Reference yield: 83.0%

2,5-dihydrofuran (1708-29-8) → cis-1,4-anhydroerythritol (4358-64-9)

Guidance literature:

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

DOI:10.3390/molecules25184307

Reference yield: 76.0%

threitol (2319-57-5,10030-58-7,188346-77-2,149-32-6) → cis-1,4-anhydroerythritol (4358-64-9)

Guidance literature:

With PEDOT⁽²⁺⁾*Cl^(1-)*FeCl₄^(1-); In toluene; for 20h; Inert atmosphere; Reflux;

DOI:10.1016/j.carres.2011.04.017

upstream raw materials:

meso-erythritol

rac-threitol

3,4-epoxytetrahydrofuran

threitol

Downstream raw materials:

2,5-dihydrofuran

C₁₄H₁₆O₇S

3-Hydroxytetrahydrofuran

tetrahydrofuran

Refernces

• 1、 Taniguchi, Kenkichi,Nanao, Hidetaka,Sato,Yamaguchi, Aritomo,Shirai, Masayuki. "Dehydration of erythritol in high-temperature carbonated water". . . Retrieved 2019.
• 2、 Childers, Karla G.,Dreher, Spencer D.,Lee, Jaemoon,Williams, J. Michael. "A practical and scaleable preparation of 1,4-anhydroerythritol". . p. 934 - 936. Retrieved 2006.
• 3、 Haines,Wells. "-". . p. 261. Retrieved 1973.
• 4、 Dra?ínsky, Martin,Frydrych, Jan,Janeba, Zlatko,Slavětínská, Lenka Po?tová. "Efficient synthesis of α-branched purine-based acyclic nucleosides: Scopes and limitations of the method". . . Retrieved 2020/10/02.