2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

Base Information

• Chemical Name: 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol
• CAS No.: 118964-46-8
• Molecular Formula: C₇₀H₇₂O₁₂
• Molecular Weight: 1105.33
• Mol file: 118964-46-8.mol

Synonyms:2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

Chemical Property of 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

There total 19 articles about 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-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:

((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol (4099-85-8,828937-29-7) → 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol (118964-46-8)

Guidance literature:

Multi-step reaction with 14 steps

1: 90 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 6 h / Ambient temperature

2: 70percent aq. acetic acid / 6 h / 80 °C

3: pyridine, DMAP / CH₂Cl₂ / 0.5 h

4: HCl-gas / CH₂Cl₂ / 18 h / 0 °C

5: CH₂Cl₂ / 3 h / Ambient temperature

6: sodium methoxide / methanol / 3 h / Ambient temperature

7: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 18 h / Ambient temperature

8: trimethylsilyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

9: silver perchlorate, molecular sieve / acetonitrile / 4 h / -40 °C

10: sodium methoxide / methanol / 2 h / Ambient temperature

11: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

12: 90 percent / lithium triethylborohydride / tetrakis(triphenylphosphine)palladium⁽⁰⁾, triphenylphosphine / dioxane; tetrahydrofuran / 1 h / Heating

13: 86 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

14: DCC, DMAP / tetrahydrofuran / 24 h

With pyridine; hydrogenchloride; dmap; chloro-trimethyl-silane; molecular sieve; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; acetic acid; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)97590-8

Reference yield:

(2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran (33019-63-5) → 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol (118964-46-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 70percent aq. acetic acid / 6 h / 80 °C

2: pyridine, DMAP / CH₂Cl₂ / 0.5 h

3: HCl-gas / CH₂Cl₂ / 18 h / 0 °C

4: CH₂Cl₂ / 3 h / Ambient temperature

5: sodium methoxide / methanol / 3 h / Ambient temperature

6: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / 18 h / Ambient temperature

7: trimethylsilyl chloride / CH₂Cl₂ / 1 h / Ambient temperature

8: silver perchlorate, molecular sieve / acetonitrile / 4 h / -40 °C

9: sodium methoxide / methanol / 2 h / Ambient temperature

10: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

11: 90 percent / lithium triethylborohydride / tetrakis(triphenylphosphine)palladium⁽⁰⁾, triphenylphosphine / dioxane; tetrahydrofuran / 1 h / Heating

12: 86 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

13: DCC, DMAP / tetrahydrofuran / 24 h

With pyridine; hydrogenchloride; dmap; chloro-trimethyl-silane; molecular sieve; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; acetic acid; dicyclohexyl-carbodiimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)97590-8

Reference yield:

Methyl 5-O-allyl-D-ribofuranoside (116490-68-7,116490-69-8,128775-32-6) → 2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol (118964-46-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / zinc chloride / 0.25 h / Ambient temperature

2: 91 percent / sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

3: mercury(II)chloride, mercury(II)oxide / acetone; H₂O / 2 h / Ambient temperature

4: sodium borohydride / methanol

5: silver perchlorate, molecular sieve / acetonitrile / 4 h / -40 °C

6: sodium methoxide / methanol / 2 h / Ambient temperature

7: sodium hydride, tetra-n-butylammonium iodide / tetrahydrofuran / Ambient temperature

8: 90 percent / lithium triethylborohydride / tetrakis(triphenylphosphine)palladium⁽⁰⁾, triphenylphosphine / dioxane; tetrahydrofuran / 1 h / Heating

9: 86 percent / pyridine, DMAP / CH₂Cl₂ / 15 h / Ambient temperature

10: DCC, DMAP / tetrahydrofuran / 24 h

With pyridine; dmap; sodium tetrahydroborate; molecular sieve; sodium methylate; silver perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium triethylborohydride; dicyclohexyl-carbodiimide; mercury dichloride; mercury(II) oxide; zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0040-4020(01)97590-8

upstream raw materials:

2,5-di-O-benzyl-β-D-ribofuranosyl 2,3,4-tri-O-benzyl-5-O-monomethoxytrityl-D-ribitol

levulinic acid

(2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran

Methyl 5-O-allyl-D-ribofuranoside

Downstream raw materials:

4-Oxo-pentanoic acid (2R,3R,4R,5R)-4-benzyloxy-2-benzyloxymethyl-5-((S)-2,3,4-tris-benzyloxy-5-hydroxy-pentyloxy)-tetrahydro-furan-3-yl ester

2,5-di-O-benzyl-3-O-levulinyl-β-ribofuranosyl 2,3,4-tri-O-benzyl-D-ribitol

Refernces

• 1、 Chan, Laval,Just, George. "A NEW APPROACH TO THE SYNTHESIS OF A DIMERIC FRAGMENT OF THE CAPSULAR POLYSACCHARIDE OF HAEMOPHILUS INFLUENZAE type b". . p. 4049 - 4052. Retrieved 2007/10/02.