2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol

Base Information

• Chemical Name: 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol
• CAS No.: 131771-48-7
• Molecular Formula: C₅₇H₅₈O₁₃
• Molecular Weight: 951.08
• Mol file: 131771-48-7.mol

Synonyms:2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol

Chemical Property of 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol

There total 6 articles about 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol 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: 85.0%

1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (6974-32-9) + 1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol (122501-70-6,131897-01-3) → 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol (131771-48-7)

Guidance literature:

With trimethylsilyl trifluoromethylmethanesulfonate; In 1,2-dichloro-ethane; Ambient temperature; a) molecular sieves 4 Angstroem, 1 h, b) 1 h;

Reference yield:

methyl α-L-ribofuranoside (52689-55-1) → 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol (131771-48-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / sodium hydride / dimethylformamide / 12 h / 20 °C

2: 1M hydrogen chloride / acetic acid; H₂O / 2 h / 100 °C

3: 87 percent / sodium borohydride / ethanol / 1 h / 50 °C

4: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

5: 85 percent / trimethylsilyl trifluoromethylmethanesulfonate / 1,2-dichloro-ethane / Ambient temperature; a) molecular sieves 4 Angstroem, 1 h, b) 1 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; trimethylsilyl trifluoromethylmethanesulfonate; sodium hydride; In ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

Reference yield:

L-ribose (41546-21-8) → 2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol (131771-48-7)

Guidance literature:

Multi-step reaction with 6 steps

1: conc. sulfuric acid / 2 h / 20 °C

2: 85 percent / sodium hydride / dimethylformamide / 12 h / 20 °C

3: 1M hydrogen chloride / acetic acid; H₂O / 2 h / 100 °C

4: 87 percent / sodium borohydride / ethanol / 1 h / 50 °C

5: 95 percent / pyridine / CH₂Cl₂ / Ambient temperature

6: 85 percent / trimethylsilyl trifluoromethylmethanesulfonate / 1,2-dichloro-ethane / Ambient temperature; a) molecular sieves 4 Angstroem, 1 h, b) 1 h

With pyridine; hydrogenchloride; sodium tetrahydroborate; trimethylsilyl trifluoromethylmethanesulfonate; sulfuric acid; sodium hydride; In ethanol; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

upstream raw materials:

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

1,3,4-tri-O-benzyl-5-O-pivaloyl-D-ribitol

methyl α-L-ribofuranoside

L-ribose

Downstream raw materials:

1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-(β-D-ribofuranosyl)-D-ribitol

1,3,4-tri-O-benzyl-2-O-<2-O-(benzyloxymethyl)-β-D-ribofuranosyl>-5-O-pivaloyl-D-ribitol

1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-<3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol

1,3,4-tri-O-benzyl-5-O-pivaloyl-2-O-<2-O-(benzyloxymethyl)-3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranosyl>-D-ribitol