3-O-benzoylcharaciol

Base Information

• Chemical Name: 3-O-benzoylcharaciol
• CAS No.: 1262324-51-5
• Molecular Formula: C₂₇H₃₄O₅
• Molecular Weight: 438.564
• Mol file: 1262324-51-5.mol

Synonyms:3-O-benzoylcharaciol

Chemical Property of 3-O-benzoylcharaciol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzoylcharaciol

There total 17 articles about 3-O-benzoylcharaciol 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: 87.0%

3-epi-characiol (1160699-98-8) + benzoic acid (65-85-0,8013-63-6) → 3-O-benzoylcharaciol (1262324-51-5)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 2.5h;

DOI:10.1021/jo1019738

Reference yield:

C16H30O4Si → 3-O-benzoylcharaciol (1262324-51-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: decane / 180 °C

2.1: decane / 180 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.25 h / 0 - 20 °C / Inert atmosphere

3.2: 0 °C

4.1: pyridinium p-toluenesulfonate

5.1: ozone; triphenylphosphine

6.1: triphenylphosphine

7.1: methyllithium

8.1: Schwartz's reagent; iodine

9.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 40 °C

9.2: 80 °C

10.1: lanthanum(III) nitrate hexahydrate / acetonitrile / 50 °C

11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide

12.1: tetrahydrofuran / -78 °C / Inert atmosphere

13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / pH 7

14.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / 110 °C

16.1: pyridine; hydrogen fluoride

17.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lithium aluminium tetrahydride; Schwartz's reagent; lanthanum(III) nitrate hexahydrate; hydrogen fluoride; methyllithium; iodine; pyridinium p-toluenesulfonate; ozone; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; decane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; 9.2: Suzuki-Miyaura cross-coupling / 17.1: Mitsunobu reaction;

DOI:10.1021/jo1019738

Reference yield:

C15H30O3Si (1114553-44-4) → 3-O-benzoylcharaciol (1262324-51-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: pyridinium p-toluenesulfonate

2.1: ozone; triphenylphosphine

3.1: triphenylphosphine

4.1: methyllithium

5.1: Schwartz's reagent; iodine

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 40 °C

6.2: 80 °C

7.1: lanthanum(III) nitrate hexahydrate / acetonitrile / 50 °C

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide

9.1: tetrahydrofuran / -78 °C / Inert atmosphere

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / pH 7

11.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide

12.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 2 h / 110 °C

13.1: pyridine; hydrogen fluoride

14.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 2.5 h / 0 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Schwartz's reagent; lanthanum(III) nitrate hexahydrate; hydrogen fluoride; methyllithium; iodine; pyridinium p-toluenesulfonate; ozone; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; 6.2: Suzuki-Miyaura cross-coupling / 14.1: Mitsunobu reaction;

DOI:10.1021/jo1019738

upstream raw materials:

C₁₅H₃₀O₃Si

C₁₈H₃₄O₃Si

C₁₇H₃₂O₄Si

C₁₈H₃₂Br₂O₃Si

Downstream raw materials:

C₂₉H₃₆O₇

15-O-acetyl-3-O-benzoylcharaciol

C₃₄H₃₈O₆