Name | Beta-D-Ribofuranose 1,2,3,5-tetraacetate |
Synonyms | TETRAACETYLRIBOSE TETRAACETYLRIBOFURANOSE 1,2,3,5-Tetra-O-acetyl- Tetraacetylribofuranose RIBOFURANOSE TETRAACETATE 1,2,3,5-Tetra-O-Acetyl-D-Ribose TETRA-O-ACETYL-B-D-RIBOFURANOSE TETRAACETYL-BETA-D-RIBOFURANOSE 1,2,3,5-tetraacetyl-beta-D-ribose TETRA-O-ACETYL-BETA-D-RIBOFURANOSE 1,2,3,5-tetra-O-acetylpentofuranose 1,2,3,5-Tetra-O-acetyl-D-ribofuranose 1,2,3,5-tetraacetyl-beta-D-ribofuranose 1,2,3,5-Tetra-O-acetyl-β-D-ribofuranose Beta-D-Ribofuranose 1,2,3,5-tetraacetate 1,2,3,5-tera-O-acetyl-beta-D-ribofuranose 1,2,3,5-tetra-O-acetyl-beta-D-ribofuranose [(2S,5R)-3,4-diacetoxy-5-(acetoxymethyl)tetrahydrofuran-2-yl] acetate |
CAS | 13035-61-5 |
EINECS | 235-898-5 |
InChI | InChI=1/C13H18O9/c1-6(14)18-5-10-11(19-7(2)15)12(20-8(3)16)13(22-10)21-9(4)17/h10-13H,5H2,1-4H3/t10-,11?,12?,13-/m1/s1 |
InChIKey | TTXVPMATRDJQIA-BKUVIOGVSA-N |
Molecular Formula | C13H18O9 |
Molar Mass | 318.28 |
Density | 1.4171 (rough estimate) |
Melting Point | 81-83°C(lit.) |
Boling Point | 417.45°C (rough estimate) |
Specific Rotation(α) | -15.4 º (c=7, MeOH) |
Flash Point | 168.5°C |
Solubility | Chloroform (Sparingly), Methanol (Slightly) |
Vapor Presure | 3.76E-06mmHg at 25°C |
Appearance | White crystalline powder |
Color | White to almost white |
BRN | 94078 |
Storage Condition | Inert atmosphere,Room Temperature |
Refractive Index | -14.5 ° (C=5, MeOH) |
MDL | MFCD00005358 |
Physical and Chemical Properties | White or off-white crystals, odorless, with a slightly bitter taste. Soluble in ethyl acetate and chloroform, slightly soluble in water. Melting point 81.5-83 °c. |
Use | As an intermediate of ribavirin |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
WGK Germany | 3 |
HS Code | 29400090 |
Raw Materials | Inosine |
introduction | tetraacetyl ribose (1,2,3,5-tetra-O-acetyl-D-ribofuranose), also known as 1,2,3,5-O-tetraacetyl-β-D-furanribose, the molecular formula is C13H18O9, which is generally prepared by degradation and acylation of nucleotides. its main industrial production method is to obtain products by acetylation, lysis and crystallization of nucleosides. In the above process, two isomers are mainly produced: 1,2,3, 5-tetra-O-acetyl-β-D-furanribose (β-tetraacetyl ribose for short) and 1,2,3, 5-Tetra-O-acetyl-α-D-furanribose (α-tetraacetyl ribose for short). |
application | tetraacetyl ribose is an important intermediate for the production of antiviral drug triazole nucleoside in the pharmaceutical industry. it is mainly used for the synthesis of broad-spectrum antiviral drug ribavirin and is also the starting material for the synthesis of nucleoside compounds. |
preparation | take a 1000mL flask, add 50g of inosine and 200ml of acetic anhydride, stir and heat to reflux, the internal liquid temperature is 120 ℃, clarify for about 60 minutes, cool to 100 ℃, add 10g of catalyst (NaSiO3 and Na2HPO4 are mixed according to 2: 1), keep the temperature at 110 ℃ for 2 hours, and connect to a Vickers fractionation column, the mixture of acetic acid and acetic anhydride was steamed under micro negative pressure, and 100ml of acid was steamed for about 100min. Continue to keep the temperature at 110 ℃ for 6 hours, and track the end point with a thin layer of color plate until triacetylinosine basically disappears. Cooling to 30 ℃, filtering, combining filtrate, vacuum evaporation of mixed acetic anhydride in a rotary evaporator, cooling the residue to 90-100 ℃, adding distilled water, 150ml, stirring, crystallization, precipitation of tetraacetyl ribose, the yield of the ribose is 94.8%. |
use | intermediates such as ribavirin. the starting material for nucleoside (nucleoside) synthesis the starting material for nucleoside synthesis; D-ribose derivatives used for ribosylation; selective 1-0-deacetylation as an intermediate for triazole nucleoside |