Tri-O-acetyl-5-deoxy-D-ribofuranose

Base Information

• Chemical Name: Tri-O-acetyl-5-deoxy-D-ribofuranose
• CAS No.: 37076-71-4
• Molecular Formula: C11H16 O7
• Molecular Weight: 260.244
• Hs Code.: 2932190090
• European Community (EC) Number: 612-957-7,253-335-1
• Nikkaji Number: J260.731J
• Mol file: 37076-71-4.mol

Synonyms:1,2,3-TA-RF;1,2,3-tri-O-acetyl-5-deoxy-D-ribofuranose

Chemical Property of Tri-O-acetyl-5-deoxy-D-ribofuranose

Chemical Property:

• Vapor Pressure: 0.00044mmHg at 25°C
• Melting Point: 58-60 °C(Solv: isopropyl ether (108-20-3))
• Boiling Point: 315.3°Cat760mmHg
• Flash Point: 135.7°C
• PSA: 88.13000
• Density: 1.23g/cm³
• LogP: 0.15770
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 260.08960285
• Heavy Atom Count: 18
• Complexity: 351

Purity/Quality:

99% ^*data from raw suppliers

(3R,4R,5R)-5-Methyltetrahydrofuran-2,3,4-triyl triacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(O1)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: C[C@@H]1[C@H]([C@H](C(O1)OC(=O)C)OC(=O)C)OC(=O)C

Technology Process of Tri-O-acetyl-5-deoxy-D-ribofuranose

There total 53 articles about Tri-O-acetyl-5-deoxy-D-ribofuranose 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: 86.68%

5'-deoxyinosine + acetic anhydride (108-24-7) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

for 9h; Reflux;

Reference yield: 86.4%

(2R,3R,4S,5R)-5-methyltetrahydrofuran-2,3,4-triol (279673-09-5,947605-23-4) + acetic anhydride (108-24-7) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

With dmap; triethylamine; at -5 - 5 ℃; for 4h;

Reference yield: 76.5%

5-deoxy-1,2,3-tri-O-acetyl-D-ribofuranose (37076-71-4) → 1,2,3-tri-O-acetyl-5-deoxy-β-D-ribofuranose (27821-07-4,27930-18-3,37076-71-4,62211-93-2,63903-44-6,76497-54-6)

Guidance literature:

In hexane; isopropyl alcohol; at -10 - 5 ℃; for 3h; Purification / work up;

upstream raw materials:

5-O-deoxy-D-ribofuranose

acetic anhydride

5′-deoxyribose

methyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside

Downstream raw materials:

5'-deoxyadenosine

1-(5-Deoxy-2,3-di-O-acetyl-α-D-ribofuranosyl)-5-fluor-uracil

1-(5-Deoxy-2,3-di-O-acetyl-β-D-ribofuranosyl)-5-fluor-uracil

doxifluridine

Refernces

• 1、 -. "Preparation method of high-purity capecitabine key intermediate". . . Retrieved 2019/03/06.
• 2、 -. "Preparation method of capecitabine intermediate". Paragraph 0007; 0016-0017. . Retrieved 2019/12/02.