(4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one
• CAS No.: 34371-14-7
• Deprecated CAS: 819081-95-3
• Molecular Formula: C5H8O4
• Molecular Weight: 132.116
• Hs Code.: 2932209090
• DSSTox Substance ID: DTXSID501308989
• Nikkaji Number: J626.035G
• Wikidata: Q27102301
• Metabolomics Workbench ID: 50847
• ChEMBL ID: CHEMBL98888
• Mol file: 34371-14-7.mol

Synonyms:2,4,5-TP;2,4,5-trihydroxypentanoic acid gamma-lactone;2-deoxy-ribono-1,4-lactone;2-deoxyribonolactone

Chemical Property of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

Chemical Property:

• Vapor Pressure: 6.9E-08mmHg at 25°C
• Refractive Index: 1.521
• Boiling Point: 395.281 °C at 760 mmHg
• PKA: 12.63±0.40(Predicted)
• Flash Point: 179.1 °C
• PSA: 66.76000
• Density: 1.439 g/cm³
• LogP: -1.34490
• Storage Temp.: ?20°C
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 132.04225873
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

98%, ^*data from raw suppliers

2-Deoxy-D-ribonic acid-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(OC1=O)CO)O
• Isomeric SMILES: C1[C@@H]([C@H](OC1=O)CO)O

Technology Process of (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one

There total 79 articles about (4S,5R)-4-hydroxy-5-(hydroxymethyl)dihydrofuran-2(3H)-one 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-(2'-Deoxy-β-D-erythro-pentafuranosyl)-7-nitroindole (201605-71-2) → 2-deoxy-D-ribonolactone (34371-14-7) + 7-nitrosoindole

Guidance literature:

In methanol; for 15h; Irradiation;

DOI:10.1002/1521-3765(20001117)6:22<4163::AID-CHEM4163>3.0.CO;2-K

Reference yield: 96.0%

3-O-benzyl-2-deoxy-D-ribonolactone (91879-31-1) → 2-deoxy-D-ribonolactone (34371-14-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 24h;

DOI:10.1021/jm034216y

Reference yield: 96.0%

3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone (146918-99-2) → 2-deoxy-D-ribonolactone (34371-14-7)

Guidance literature:

With trifluoroacetic acid; In chloroform; water; at 70 ℃; for 10h;

DOI:10.1080/00397919908086215

upstream raw materials:

D-Glucose

L-Lysine hydrochloride

D-2-deoxyribose

2-Bromo-2-deoxy-D-arabinono-γ-lactone

Downstream raw materials:

D-erythro-2-deoxy-pentonic acid-(N'-phenyl-hydrazide)

(5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one

3,5-di-O-(tert-butyldimethylsilyl)-2-deoxy-D-ribono-1,4-lactone

3,4-O-(R)-benzylidene-2-deoxy-D-erythro-ribono-1,5-lactone

Refernces

• 1、 Chbib, Christiane. "Synthesis of isomeric analogues of S-ribosylhomocysteine analogues with homocysteine unit attached to C2 of ribose". . p. 1681 - 1685. Retrieved 2017.
• 2、 Scott Daniels,Gates, Kent S.,Tronche, Christopher,Greenberg, Marc M.. "Direct evidence for bimodal DNA damage induced by tirapazamine". . p. 1254 - 1257. Retrieved 1998.
• 3、 Chatgilialoglu, Chryssostomos,Gimisis, Thanasis. "Fate of the C-1′ peroxyl radical in the 2′-deoxyuridine system". . p. 1249 - 1250. Retrieved 1998.
• 4、 Wagner, J. Richard,Decarroz, Chantal,Berger, Maurice,Cadet, Jean. "Hydroxyl-radical-induced decomposition of 2'-deoxycytidine in aerated aqueous solutions". . p. 4101 - 4110. Retrieved 1999.
• 5、 Matsumoto,Ebata,Koseki,Okano,Kawakami,Matsushita. "Short synthesis of (3S,4R)- and (3R,4R)-3-hydroxy-4-hydroxymethyl-4-butanolides, two lactones from levoglucosenone". . p. 670 - 672. Retrieved 1995.
• 6、 Emanuel, Calvin J.,Newcomb, Martin,Ferreri, Carla,Chatgilialoglu, Chryssostomos. "Kinetics of 2'-deoxyuridin-1'-yl radical reactions". . p. 2927 - 2928. Retrieved 1999.
• 7、 -. "METHOD FOR PRODUCING SUGAR". Paragraph 0047. . Retrieved 2020/10/21.
• 8、 Grebenovsky, Nikolai,Goldau, Thomas,Bolte, Michael,Heckel, Alexander. "Light Regulation of DNA Minicircle Dimerization by Utilizing Azobenzene C-Nucleosides". supporting information. p. 3425 - 3428. Retrieved 2018/02/15.