5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside

Base Information

• Chemical Name: 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside
• CAS No.: 115079-06-6
• Molecular Formula: C₁₆H₂₂O₄
• Molecular Weight: 278.348
• Mol file: 115079-06-6.mol

Synonyms:5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside

Chemical Property of 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside

There total 11 articles about 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside 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:

3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (19029-63-1) → 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside (115079-06-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

2: tetrahydrofuran / 13 h / 22 °C

3: H₂ / Pd/C / methanol / 1500.1 Torr

4: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

5: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

6: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C

7: 1.) NaH; 2.) CS₂; 3.) methyl iodide; 4.) Bu₃SnH / 4.) AIBN

8: 77 percent / sodium / NH₃; tetrahydrofuran / 0.05 h / -50 °C

9: 1.) DMSO, pyridine, CF₃CO₂H, DCC; 2.) ether, methanol, oxalic acid / 1.) toluene, 22 deg C, 18 h; 2.) toluene, 1 h

10: 1.) KMnO₄, phosphate buffer / 1.) tert-butyl alcohol-water, 22 deg C, 10 min; 2.) methanol-ether, 22 deg C

With pyridine; lead(IV) acetate; methanol; carbon disulfide; potassium permanganate; lithium aluminium tetrahydride; phosphate buffer; diethyl ether; hydrogen; tri-n-butyl-tin hydride; sodium; oxalic acid; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a024

Reference yield:

1,2:5,6-di-O-isopropylidene-3-deoxy-3-(methoxycarbonyl-methyl)-α-D-allofuranoside (18427-18-4) → 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside (115079-06-6)

Guidance literature:

Multi-step reaction with 11 steps

1: AcOH/water / 37 h / 22 °C

2: 1.) lead tetraacetate; 2.) K₂CO₃ / 1.) CH₂Cl₂, 22 deg C, 2 h; 2.) CH₂Cl₂, 1 h

3: tetrahydrofuran / 13 h / 22 °C

4: H₂ / Pd/C / methanol / 1500.1 Torr

5: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

6: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

7: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C

8: 1.) NaH; 2.) CS₂; 3.) methyl iodide; 4.) Bu₃SnH / 4.) AIBN

9: 77 percent / sodium / NH₃; tetrahydrofuran / 0.05 h / -50 °C

10: 1.) DMSO, pyridine, CF₃CO₂H, DCC; 2.) ether, methanol, oxalic acid / 1.) toluene, 22 deg C, 18 h; 2.) toluene, 1 h

11: 1.) KMnO₄, phosphate buffer / 1.) tert-butyl alcohol-water, 22 deg C, 10 min; 2.) methanol-ether, 22 deg C

With pyridine; lead(IV) acetate; methanol; carbon disulfide; potassium permanganate; lithium aluminium tetrahydride; phosphate buffer; diethyl ether; water; hydrogen; tri-n-butyl-tin hydride; sodium; oxalic acid; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a024

Reference yield:

3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose (56777-87-8) → 5-C-benzyl-3-C-<(methoxycarbonyl)methyl>-2,3,5-trideoxy-β-D-methylribofuranoside (115079-06-6)

Guidance literature:

Multi-step reaction with 9 steps

1: tetrahydrofuran / 13 h / 22 °C

2: H₂ / Pd/C / methanol / 1500.1 Torr

3: 1.) p-toluenesulfonic acid; 2.) lithium aluminum hydride / 1.) methanol-water, 8 h; 2.) THF, reflux, 1 h

4: 90 percent / sodium hydride / dimethylformamide / 4 h / 22 °C

5: 73 percent / p-toluenesulfonic acid / methanol / 24 h / 22 °C

6: 1.) NaH; 2.) CS₂; 3.) methyl iodide; 4.) Bu₃SnH / 4.) AIBN

7: 77 percent / sodium / NH₃; tetrahydrofuran / 0.05 h / -50 °C

8: 1.) DMSO, pyridine, CF₃CO₂H, DCC; 2.) ether, methanol, oxalic acid / 1.) toluene, 22 deg C, 18 h; 2.) toluene, 1 h

9: 1.) KMnO₄, phosphate buffer / 1.) tert-butyl alcohol-water, 22 deg C, 10 min; 2.) methanol-ether, 22 deg C

With pyridine; methanol; carbon disulfide; potassium permanganate; lithium aluminium tetrahydride; phosphate buffer; diethyl ether; hydrogen; tri-n-butyl-tin hydride; sodium; oxalic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; methyl iodide; palladium on activated charcoal; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; methanol; ammonia; N,N-dimethyl-formamide;

DOI:10.1021/ja00222a024

upstream raw materials:

diazomethane

((2R,3S,5R)-5-Methoxy-2-phenethyl-tetrahydro-furan-3-yl)-acetaldehyde

3-C-(carbomethoxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

1,2:5,6-di-O-isopropylidene-3-deoxy-3-(methoxycarbonyl-methyl)-α-D-allofuranoside