methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate

Base Information

• Chemical Name: methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate
• CAS No.: 68673-84-7
• Molecular Formula: C12H16O9
• Molecular Weight: 304.25000
• DSSTox Substance ID: DTXSID90445522
• Nikkaji Number: J2.563.199D
• Wikidata: Q82263966
• Mol file: 68673-84-7.mol

Synonyms:68673-84-7;methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate;(2S,3R,4S,5S)-5-(Methoxycarbonyl)tetrahydrofuran-2,3,4-triyl triacetate;FT-0674416;DTXSID90445522;WKPDVIUFXMUXNU-DTHBNOIPSA-N;1-O,2-O,3-O-Triacetyl-beta-D-ribofuranuronic acid methyl ester

Chemical Property of methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate

Chemical Property:

• PSA: 114.43000
• LogP: -0.68920
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 304.07943208
• Heavy Atom Count: 21
• Complexity: 444

Purity/Quality:

99% ^*data from raw suppliers

β-D-RibofuranuronicAcidMethylEsterTriacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1C(C(OC1C(=O)OC)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)O[C@H]1[C@H]([C@@H](O[C@@H]1C(=O)OC)OC(=O)C)OC(=O)C
• Uses: β-D-Ribofuranuronic Acid Methyl Ester Triacetate can be used in the synthesis of tritiated 2-chloro-N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide, a potent, selective A3 adenosine receptor agonist, a radiolabeling agent. Used in the synthesis of tritiated 2-chloro-N6-(3-iodobenzyl)adenosine-5''-N-methyluronamide, a potent, selective A3 adenosine receptor agonist, a radiolabeling agent.

Technology Process of methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate

There total 4 articles about methyl (2S,3S,4R,5S)-3,4,5-triacetyloxyoxolane-2-carboxylate 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: 92.0%

methanol (67-56-1) + C11H14O9 (1012864-56-0) → methyl 1,2,3-tri-O-acetyl-β-D-ribofuronate (68673-84-7)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; at 25 ℃; for 4h;

DOI:10.1016/j.tet.2009.08.057

Reference yield:

Methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-xylouronate (114194-86-4) + acetic anhydride (108-24-7) → Methyl 1,2,3-tri-O-acetyl-β-D-xyluronate (68673-84-7,114249-45-5) + Methyl 1,2,3-tri-O-acetyl-α-D-xyluronate (68673-84-7,114249-45-5)

Guidance literature:

With sulfuric acid; In acetic acid; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1007/BF00759055

Reference yield:

Methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-xylouronate (114194-86-4) + acetic anhydride (108-24-7) → Methyl 1,2,3-tri-O-acetyl-β-D-xyluronate (68673-84-7,114249-45-5) + Methyl 1,2,3-tri-O-acetyl-α-D-xyluronate (68673-84-7,114249-45-5)

Guidance literature:

With sulfuric acid; In acetic acid; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1007/BF00759055

upstream raw materials:

Methyl 3-O-acetyl-1,2-O-isopropylidene-α-D-xylouronate

acetic anhydride

methanol

C₁₁H₁₄O₉

Downstream raw materials:

methyl 1-[2-(phenylethynyl)adenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate

methyl 1-[N⁶-benzyl-2-chloroadenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate

methyl 1-[N⁶-(benzyl)adenin-9-yl]-2,3-di-O-acetyl-β-D-ribofuronate

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