2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one

Base Information

• Chemical Name: 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one
• CAS No.: 264603-21-6
• Molecular Formula: C₂₄H₃₆O₅Si
• Molecular Weight: 432.632
• Mol file: 264603-21-6.mol

Synonyms:2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one

Chemical Property of 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one

There total 6 articles about 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one 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: 92.0%

2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one (264603-33-0) → 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one (264603-21-6)

Guidance literature:

With pyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃;

DOI:10.1021/ol005605e

Reference yield:

(R)-1-benzyloxypent-4-en-2-ol (58931-16-1,88981-35-5,110339-28-1) → 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one (264603-21-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium hydride / tetrahydrofuran / 0.25 h / 0 °C

1.2: 84 percent / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / osmium tetraoxide; 4-methylmorpholine N-oxide monohydrate; sodium periodate / H₂O; tetrahydrofuran / 18 h

3.1: diisopropyl amine; lithium chloride; n-butyl lithium / tetrahydrofuran / 2 h / -78 °C

3.2: 73 percent / tetrahydrofuran / 0.33 h / -78 °C

4.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 °C

5.1: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; pyridine / H₂O; CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; n-butyllithium; potassium hydride; 4-methylmorpholine 4-oxide monohydrate; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; dichloromethane; water; 1.1: Etherification / 1.2: Etherification / 2.1: Oxidation / 3.1: Metallation / 3.2: Addition / 4.1: Substitution / 5.1: Oxidation;

DOI:10.1021/ol005605e

Reference yield:

(R)-benzyl glycidol (14618-80-5) → 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one (264603-21-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / copper(I) iodide / tetrahydrofuran / 1.5 h / -30 °C

2.1: potassium hydride / tetrahydrofuran / 0.25 h / 0 °C

2.2: 84 percent / tetrahydrofuran / 0 - 20 °C

3.1: 90 percent / osmium tetraoxide; 4-methylmorpholine N-oxide monohydrate; sodium periodate / H₂O; tetrahydrofuran / 18 h

4.1: diisopropyl amine; lithium chloride; n-butyl lithium / tetrahydrofuran / 2 h / -78 °C

4.2: 73 percent / tetrahydrofuran / 0.33 h / -78 °C

5.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / -10 °C

6.1: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone; pyridine / H₂O; CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; potassium hydride; 4-methylmorpholine 4-oxide monohydrate; diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; dichloromethane; water; 1.1: Ring cleavage / 2.1: Etherification / 2.2: Etherification / 3.1: Oxidation / 4.1: Metallation / 4.2: Addition / 5.1: Substitution / 6.1: Oxidation;

DOI:10.1021/ol005605e

upstream raw materials:

2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one

(R)-1-benzyloxypent-4-en-2-ol

(R)-benzyl glycidol

(3R)-4-benzyloxy-3-(4-methoxy-benzyloxy)-butyraldehyde

Downstream raw materials:

2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one

(6R,8R,10S)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-butyl)-1,7-dioxa-spiro[5.5]undec-2-en-4-one

(6R,8R,10R)-8-benzyloxymethyl-10-(tert-butyl-dimethyl-silanyloxy)-2-(2-hydroxy-butyl)-1,7-dioxa-spiro[5.5]undec-2-en-4-one