methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate

Base Information

• Chemical Name: methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate
• CAS No.: 93215-19-1
• Molecular Formula: C₅₈H₅₆O₂₂
• Molecular Weight: 1105.07
• Mol file: 93215-19-1.mol

Synonyms:methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate

Chemical Property of methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate

There total 7 articles about methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate 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: 43.0%

3-O-acetyl-5-O-benzoyl-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-D-ribofuranosyl bromide (93245-42-2) + methyl (methyl 8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid)onate (94528-57-1) → methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate (93215-19-1)

Guidance literature:

With calcium sulfate; silver trifluoromethanesulfonate; In dichloromethane; at -15 ℃; for 0.333333h;

DOI:10.1016/0008-6215(84)85223-4

Reference yield:

benzyl 5-O-benzoyl-β-D-ribofuranoside (93215-12-4) → methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate (93215-19-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) dibutyltin oxide / 1.) toluene, reflux, 3 h, 2.) N,N-dimethylformamide, 48 h, 70 deg C

2: 81 percent / silver triflate, Drierite / CH₂Cl₂ / 0.17 h / -25 °C

3: 65 percent / hydrogen, palladium oxide / methanol; ethyl acetate / Ambient temperature

4: 97 percent / pyridine / 3 h / Ambient temperature

5: 162 mg / TiBr₄ / CH₂Cl₂ / 18 h / 4 °C

6: 43 percent / silver triflate, Drierite / CH₂Cl₂ / 0.33 h / -15 °C

With pyridine; palladium(II) oxide; calcium sulfate; hydrogen; silver trifluoromethanesulfonate; titanium(IV) bromide; di(n-butyl)tin oxide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(84)85223-4

Reference yield:

benzyl 5-O-benzoyl-3-O-benzyl-β-D-ribofuranoside (93245-41-1) → methyl -8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate (93215-19-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / silver triflate, Drierite / CH₂Cl₂ / 0.17 h / -25 °C

2: 65 percent / hydrogen, palladium oxide / methanol; ethyl acetate / Ambient temperature

3: 97 percent / pyridine / 3 h / Ambient temperature

4: 162 mg / TiBr₄ / CH₂Cl₂ / 18 h / 4 °C

5: 43 percent / silver triflate, Drierite / CH₂Cl₂ / 0.33 h / -15 °C

With pyridine; palladium(II) oxide; calcium sulfate; hydrogen; silver trifluoromethanesulfonate; titanium(IV) bromide; In methanol; dichloromethane; ethyl acetate;

DOI:10.1016/0008-6215(84)85223-4

upstream raw materials:

3-O-acetyl-5-O-benzoyl-2-O-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-D-ribofuranosyl bromide

methyl (methyl 8-O-benzyl-4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid)onate

benzyl 5-O-benzoyl-β-D-ribofuranoside

benzyl 5-O-benzoyl-3-O-benzyl-β-D-ribofuranoside

Downstream raw materials:

methyl -4,5-O-carbonyl-3-deoxy-β-D-manno-2-octulopyranosid>onate