2-C-Methyl-D-ribonoic acid-1,4-Lactone

2-C-Methyl-D-ribonoic acid-1,4-Lactone - Names and Identifiers

Name	2-C-Methyl-D-ribono-1,4-lactone
Synonyms	EOS-60512 2-C-Methyl- 2-C-metylribono-γ-lactone Ascorbic Acid Impurity 17 2-C-Methyl-D-ribono-1,4-lactone 2-C-Methyl-D-ribonoic acid-1,4-Lactone 2-C-Methyl-D-ribonic Acid gamma-Lactone 3,4-Dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one 3,4-dihydroxy-5-(hydroxymethyl)-3-methyl-2-oxolanone (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyloxolan-2-one (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one 3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one (non-preferred name) (3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-3-methyldihydrofuran-2(3H)-one (non-preferred name)
CAS	492-30-8
EINECS	610-448-4
InChI	InChI=1/C6H10O5/c1-6(10)4(8)3(2-7)11-5(6)9/h3-4,7-8,10H,2H2,1H3/t3-,4-,6-/m1/s1

2-C-Methyl-D-ribonoic acid-1,4-Lactone - Physico-chemical Properties

Molecular Formula	C6H10O5
Molar Mass	162.14
Density	1.512±0.06 g/cm3(Predicted)
Melting Point	150-160°C
Boling Point	338.3±11.0 °C(Predicted)
Flash Point	145.586°C
Solubility	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Vapor Presure	0mmHg at 25°C
Appearance	Solid
Color	White to Off-White
pKa	12.12±0.60(Predicted)
Storage Condition	Sealed in dry,Store in freezer, under -20°C
Refractive Index	1.551

2-C-Methyl-D-ribonoic acid-1,4-Lactone - Reference Information

pharmaceutical intermediates

2-C-methyl-D-ribono-1, 4-lactone is an important pharmaceutical intermediate that can be used to prepare nucleoside drugs. Nucleoside drugs have broad application fields in anti-virus and anti-tumor, such as anti-hepatitis C virus (HCV) drugs. Nucleoside drugs are important drugs for the treatment of viral infectious diseases, tumors and AIDS. Nearly 50% of all antiviral drugs currently used are nucleoside drugs. Anti-tumor drugs such as cytarabine and deoxyfluorouridine (Doxifluridine) also belong to nucleoside. Nucleoside drugs successfully developed in recent years include HIV reverse transcriptase inhibitors zidovudine, dideoxycytidine (Didanosine,ddI), zacitabine (Zalcitabine,ddC), stavudine (Stavudine, d4T), lamivudine (Lamivudine,3TC) for the treatment of AIDS; Acyclovir and famciclovir for the treatment of herpes virus infection; Ara adenosine (Vidarabine,Ara-A) for the treatment of herpes simplex and encephalitis, and ribavirin for the treatment of influenza, herpes virus infection and hepatitis. Nucleotide drugs, such as polyinosinic cells, can efficiently induce the production of interferon, and have broad-spectrum antiviral and enhance the body's immunity.

preparation method

at present, there are three main preparation methods of 2-C-methyl-D-ribono-1, 4-lactone known, which are:
the first method (Hong-Se 2,Han-Young K.Tetrahedron,2010,66:4307-4317) uses D-glucose as the starting material, under the action of ethanol, acetic acid and dimethylamine, isomerism is converted into D-fructose, and then the crude product is obtained through multiple steps such as calcium salt formation, ion exchange, dissolution, vacuum distillation and recrystallization. Due to the cumbersome and complicated operation of this method, it is difficult to realize industrialization.
the second method (Hotchkiss David,Fleet George,Heinz Thomas,et al.WO 2007025304) uses D-fructose as raw material, first reacts with dibenzylamine, then carries out internal esterification reaction. after 51h reaction, the yield is 13%. Although the method has fewer reaction steps, the reaction time is longer and the yield is lower.
the third method (Richard S,Nary an C,Frank W.US:7598373B2) uses D-fructose as raw material to obtain the product after calcium salt formation, CO2 removal of calcium ions, pH adjustment, reduced pressure water removal, tetrahydrofuran extraction, reduced pressure distillation and recrystallization, in which the reaction time is about 12 hours and the yield is 16.9%. Compared with method 2, the reaction time of this method is greatly reduced and the yield is slightly improved, but the process is complicated and the operation difficulty is slightly increased.

Last Update：2024-04-09 20:52:54