Methyl-2-deoxy-D-ribofuranoside diacetate

Base Information

• Chemical Name: Methyl-2-deoxy-D-ribofuranoside diacetate
• CAS No.: 151767-35-0
• Molecular Formula: C10H16O6
• Molecular Weight: 232.233
• DSSTox Substance ID: DTXSID90557497
• Nikkaji Number: J1.384.086E
• Mol file: 151767-35-0.mol

Synonyms:151767-35-0;Methyl-2-deoxy-D-ribofuranoside diacetate;Methyl 3,5-di-O-acetyl-2-deoxy-D-ribofuranoside;[(2R,3S)-3-acetyloxy-5-methoxyoxolan-2-yl]methyl acetate;SCHEMBL9290126;DTXSID90557497;1H-Indazole-3,4-dicarboxylicacid4-methylester;W-201351;Methyl 3,5-di-O-acetyl-2-deoxy-D-erythro-pentofuranoside;3-Acetoxy-5-methoxy-tetrahydrofuran-2-yl Methyl Ester Acetic Acid

Chemical Property of Methyl-2-deoxy-D-ribofuranoside diacetate

Chemical Property:

• Boiling Point: 313.041 °C at 760 mmHg
• Flash Point: 115.491 °C
• PSA: 71.06000
• Density: 1.239 g/cm³
• LogP: 0.24260
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 232.09468823
• Heavy Atom Count: 16
• Complexity: 264

Purity/Quality:

98% ^*data from raw suppliers

METHYL-2-DEOXY-D-RIBOFURANOSIDE DIACETATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(CC(O1)OC)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H](CC(O1)OC)OC(=O)C
• Uses: Acetic Acid 3-acetoxy-5-methoxy-tetrahydrofuran-2-yl Methyl Ester is used as a reactant in the synthesis of deoxyribose related disaccharide nucleoside and its phosphoramidite.

Technology Process of Methyl-2-deoxy-D-ribofuranoside diacetate

There total 5 articles about Methyl-2-deoxy-D-ribofuranoside diacetate 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: 98.0%

acetic anhydride (108-24-7) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside (151767-35-0)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 17h; Inert atmosphere;

DOI:10.1002/ejoc.201901465

Reference yield: 85.0%

acetyl chloride (75-36-5) + 1-O-methyl-2-deoxy-D-ribofuranoside (51255-17-5,51255-18-6,60134-26-1,89577-26-4,96038-80-1,96039-31-5,144301-84-8,144301-85-9) → 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside (151767-35-0)

Guidance literature:

With pyridine; In dichloromethane; at -30 - 20 ℃; for 7.97h; Inert atmosphere; Industry scale;

Reference yield:

D-2-deoxyribose (452-51-7,13046-70-3,29780-54-9,36792-87-7,36792-88-8,113890-35-0,113890-38-3) → 3,5-di-O-acetyl-2-deoxy-α/β-D-ribofuranoside (151767-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 0.5percent HCl / 1 h / Ambient temperature

2: pyridine / Ambient temperature

With pyridine; hydrogenchloride;

DOI:10.1021/jm00391a036

upstream raw materials:

methanol

2-Deoxy-D-ribose

acetic anhydride

1-O-methyl-2-deoxy-D-ribofuranoside

Downstream raw materials:

Acetic acid (2R,3S)-2-acetoxymethyl-5-phenylsulfanyl-tetrahydro-furan-3-yl ester

1-(3,5-di-O-acetyl-2-deoxy-D-ribofuranosyl)-5-azacytosine

4-amino-1-(O³,O⁵-diacetyl-β-D-erythro-2-deoxy-pentofuranosyl)-1H-[1,3,5]triazin-2-one

1,3,5-tri-O-acetyl-2-deoxyribose