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

Base Information

• Chemical Name: 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one
• CAS No.: 264603-33-0
• Molecular Formula: C₃₂H₄₄O₆Si
• Molecular Weight: 552.783

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

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

Chemical Property:

Purity/Quality:

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

There total 5 articles about 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-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: 70.0%

t-butyldimethylsiyl triflate (69739-34-0) + 2-[(4R)-5-benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one (264603-20-5) → 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one (264603-33-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -10 ℃; for 4h;

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-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one (264603-33-0)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/ol005605e

Reference yield:

(R)-benzyl glycidol (14618-80-5) → 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one (264603-33-0)

Guidance literature:

Multi-step reaction with 5 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

With 2,6-dimethylpyridine; sodium periodate; copper(l) iodide; osmium(VIII) oxide; n-butyllithium; potassium hydride; 4-methylmorpholine 4-oxide monohydrate; diisopropylamine; 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;

DOI:10.1021/ol005605e

upstream raw materials:

t-butyldimethylsiyl triflate

2-[(4R)-5-benzyloxy-2-hydroxy-4-(4-methoxy-benzyloxy)-pentyl]-6-methyl-pyran-4-one

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

(R)-benzyl glycidol

Downstream raw materials:

(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

(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

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

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

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