[(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-methoxyoxolan-2-yl]methyl benzoate

Base Information

• Chemical Name: [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-methoxyoxolan-2-yl]methyl benzoate
• CAS No.: 68045-07-8
• Molecular Formula: C27H24O8
• Molecular Weight: 476.483
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID30448254
• Wikidata: Q72509820

Synonyms:1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribose;SCHEMBL1738477;DTXSID30448254;BTKQRBSDABCRCX-DVAKJLRASA-N;2-O-methyl-1,3,5-tri-O-benzoyl-alpha-D-ribose;W-203511

Chemical Property of [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-methoxyoxolan-2-yl]methyl benzoate

Chemical Property:

• Boiling Point: 598.8±50.0 °C(Predicted)
• PSA: 97.36000
• Density: 1.32±0.1 g/cm3(Predicted)
• LogP: 3.66590
• Storage Temp.: 2-8°C
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 11
• Exact Mass: 476.14711772
• Heavy Atom Count: 35
• Complexity: 706

Purity/Quality:

97% ^*data from raw suppliers

1,3,5-Tri-O-benzoyl-2-O-methyl-D-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1C(C(OC1OC(=O)C2=CC=CC=C2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Isomeric SMILES: CO[C@@H]1[C@@H]([C@H](O[C@@H]1OC(=O)C2=CC=CC=C2)COC(=O)C3=CC=CC=C3)OC(=O)C4=CC=CC=C4
• Uses: 1,3,5-Tri-O-benzoyl-2-O-methyl-α-D-ribofuranose is used as a reactant in the preparation of 2''-O-methylpyrimidine ribonucleosides via stereoselective Vorbruggen glycosidation of pyrimidines. It is also used as a reactant in solid-phase synthesis, fluorescence, and ambiguous base pairing of canonical DNA nucleobases containing benzotriazole and 1,2,3-triazolo[4,5-d]pyrimidine.

Technology Process of [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-methoxyoxolan-2-yl]methyl benzoate

There total 2 articles about [(2R,3R,4R,5R)-3,5-dibenzoyloxy-4-methoxyoxolan-2-yl]methyl benzoate 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: 74.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 1,3,5-tri-O-benzoyl-α-D-ribofuranoside (22224-41-5) → 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8,38791-39-8)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃;

DOI:10.1021/jo00341a005

Reference yield:

→ 1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8,38791-39-8)

Guidance literature:

Ribofuranose 5a, CH2N2, BF3;

Reference yield: 75.0%

1,3,5-tri-O-benzoyl-2-O-methyl-α-D-ribofuranose (68045-07-8,38791-39-8) + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → 3',5'-di-O-benzoyl-2'-O-methyluridine (79816-14-1) + C24H22N2O8

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; for 0.5h; Yields of byproduct given; Ambient temperature;

DOI:10.1002/jhet.5570310412

upstream raw materials:

diazomethane

1,3,5-tri-O-benzoyl-α-D-ribofuranoside

Downstream raw materials:

1-(3,5-di-O-benzoyl-2-O-methyl-β-D-ribofuranosyl)-2-thio-4-(1H,3H)-pyrimidinone

N⁴-benzoyl-3',5'-di-O-benzoyl-2'-O-methylcytidine

3',5'-di-O-benzoyl-2'-O-methyl-5-nitrouridine

3',5'-di-O-benzoyl-2'-O-methyl-5-trifluoromethyluridine

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