1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE

Base Information

• Chemical Name: 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE
• CAS No.: 171866-30-1
• Molecular Formula: C26H22O8
• Molecular Weight: 462.456
• Mol file: 171866-30-1.mol

Synonyms:1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE;alpha-L-Ribofuranose 1,3,5-tribenzoate

Chemical Property of 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE

Chemical Property:

• Boiling Point: 629.6±55.0 °C(Predicted)
• PKA: 12.35±0.70(Predicted)
• PSA: 108.36000
• Density: 1.37±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 3.01180

Purity/Quality:

97%min ^*data from raw suppliers

1-3-5-Tri-O-benzoyl-α-L-ribofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,3,5-TRI-O-BENZOYL-ALPHA-L-RIBOFURANOSE

There total 19 articles about 1,3,5-TRI-O-BENZOYL-ALPHA-L-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: 57.0%

2,3,5-tri-O-benzoyl-α-L-ribofuranosyl bromide + 2,3,5-tri-O-benzoyl-β-L-ribofuranosyl bromide → 1,3,5-Tri-O-benzoyl-α-L-ribofuranose (171866-30-1)

Guidance literature:

With water; In acetonitrile; at 0 ℃; for 3.5h;

Reference yield:

benzoyl chloride (98-88-4) → 1,3,5-Tri-O-benzoyl-α-L-ribofuranose (171866-30-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / pyridine / 3 h / Ambient temperature

2: 1percent HCl / methanol / 30 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: AcOH, conc. H₂SO₄ / Ambient temperature

5: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

With pyridine; hydrogenchloride; sulfuric acid; water; acetic acid; acetyl chloride; In methanol;

DOI:10.1021/jm960098l

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose (166411-40-1) → 1,3,5-Tri-O-benzoyl-α-L-ribofuranose (171866-30-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / NaBH₄, H₂O / ethanol / 4 h / Ambient temperature

2: 98 percent / pyridine / 3 h / Ambient temperature

3: 1percent HCl / methanol / 30 h / Ambient temperature

4: pyridine / 3 h / Ambient temperature

5: AcOH, conc. H₂SO₄ / Ambient temperature

6: 1.) HCl(g), AcCl, 2.) H₂O / 1.) CH₂Cl₂, 0 deg C, 2.) CH₃CN

With pyridine; hydrogenchloride; sodium tetrahydroborate; sulfuric acid; water; acetic acid; acetyl chloride; In methanol; ethanol;

DOI:10.1021/jm960098l

upstream raw materials:

1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose

1-O-methyl-2,3,5-tri-O-benzoyl-L-ribofuranose

1-O-benzyl-3,4-O-isopropylidene-β-L-ribopyranose

benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside

Downstream raw materials:

1,3,5-tri-O-benzoyl-2-O-(2-imidazolylsulfonyl)-α-L-ribofuranose

clevudine

1-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-L-arabinofuranosyl)thymine

1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-L-arabinofuranosyl)thymine

Refernces

• 1、 -. "2'-deoxy-L-nucleosides". Page/Page column 37. . Retrieved 2010/02/11.
• 2、 Du, Jinfa,Choi, Yongseok,Lee, Kyeong,Chun, Byoung K.,Hong, Joon H.,Chu, Chung K.. "A practical synthesis of L-FMAU from L-arabinose". . p. 187 - 195. Retrieved 2007/10/03.