<2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate

Base Information

• Chemical Name: <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate
• CAS No.: 114644-91-6
• Molecular Formula: C₅₀H₄₂O₁₁
• Molecular Weight: 818.877

Synonyms:<2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate

Chemical Property of <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate

There total 15 articles about <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate 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:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate (114644-91-6)

Guidance literature:

Multi-step reaction with 14 steps

1: K₂CO₃ / acetone / 16 h / Heating

2: 95 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

3: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 66 percent / POCl₃ / 2.5 h / 97 °C

5: 92 percent / Yb(fod)3 / CDCl₃ / 84 h / 55 °C

6: 70 percent / CuI, dimethylsulfide / tetrahydrofuran / 1.5 h / -78 °C

7: NaIO₄, OsO₄ / dioxane; H₂O; tetrahydrofuran / 40 h

8: lithium tris(3-ethyl-3-pentyloxy)aluminum hydride / tetrahydrofuran / 2 h / -78 °C

11: 1.) hexamethyldisilazane, butyllithium, 2.) hexamethylphosphoramide / 1.) oxolane - hexane, -78 deg C, 2.) -78 deg C, 15 min.

12: palladium (II) acetate / acetonitrile / 24 h

13: diisobutyl aluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

14: pyridine / 10 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; dimethylsulfide; palladium diacetate; diisobutylaluminium hydride; potassium carbonate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; chloroform-d1; hexane; dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0008-6215(00)90895-4

Reference yield:

methyl 3,5-bis(benzyloxy)benzoate (58605-10-0) → <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate (114644-91-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 95 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

2: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

3: 66 percent / POCl₃ / 2.5 h / 97 °C

4: 92 percent / Yb(fod)3 / CDCl₃ / 84 h / 55 °C

5: 70 percent / CuI, dimethylsulfide / tetrahydrofuran / 1.5 h / -78 °C

6: NaIO₄, OsO₄ / dioxane; H₂O; tetrahydrofuran / 40 h

7: lithium tris(3-ethyl-3-pentyloxy)aluminum hydride / tetrahydrofuran / 2 h / -78 °C

10: 1.) hexamethyldisilazane, butyllithium, 2.) hexamethylphosphoramide / 1.) oxolane - hexane, -78 deg C, 2.) -78 deg C, 15 min.

11: palladium (II) acetate / acetonitrile / 24 h

12: diisobutyl aluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

13: pyridine / 10 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; dimethylsulfide; palladium diacetate; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; chloroform-d1; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0008-6215(00)90895-4

Reference yield:

3,5-dibenzyloxybenzyl alcohol (24131-31-5) → <2-(3-acetyl-1,5-anhydro-4,6-di-O-benzoyl-2-deoxy-DL-arabino-hex-1-enit-3-yl)-3,5-dibenzoyloxyphenyl>methyl benzoate (114644-91-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 100 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

2: 66 percent / POCl₃ / 2.5 h / 97 °C

3: 92 percent / Yb(fod)3 / CDCl₃ / 84 h / 55 °C

4: 70 percent / CuI, dimethylsulfide / tetrahydrofuran / 1.5 h / -78 °C

5: NaIO₄, OsO₄ / dioxane; H₂O; tetrahydrofuran / 40 h

6: lithium tris(3-ethyl-3-pentyloxy)aluminum hydride / tetrahydrofuran / 2 h / -78 °C

9: 1.) hexamethyldisilazane, butyllithium, 2.) hexamethylphosphoramide / 1.) oxolane - hexane, -78 deg C, 2.) -78 deg C, 15 min.

10: palladium (II) acetate / acetonitrile / 24 h

11: diisobutyl aluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

12: pyridine / 10 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)ytterbium; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; dimethylsulfide; palladium diacetate; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; pyridine; chloroform-d1; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/S0008-6215(00)90895-4

upstream raw materials:

acetic anhydride

C₄₈H₄₀O₁₀

1-carbomethoxy-3,5-dihydroxybenzene

methyl 3,5-bis(benzyloxy)benzoate

Downstream raw materials:

(3R,4S,5S,6R)-2-(2,4-Bis-benzyloxy-6-hydroxymethyl-phenyl)-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-3,4,5-triol

<3,5-dibenzoyloxy-2-(methyl-3-O-acetyl-4,6-di-O-benzoyl-DL-glucopyuranosid-1-yl)phenyl>methyl benzoate

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