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

Base Information

Chemical Name:2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one
CAS No.:264603-22-7
Molecular Formula:C₂₇H₄₂O₆Si
Molecular Weight:490.712
Hs Code.:

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

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

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

There total 7 articles about 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-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: 63.0%

: 123-38-6
propionaldehyde

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

: 264603-22-7
2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one

Guidance literature:: 2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-methyl-pyran-4-one; With n-butyllithium; diisopropylamine; lithium chloride; In tetrahydrofuran; at -98 ℃; for 0.666667h;

propionaldehyde; In tetrahydrofuran; at -98 ℃; for 0.333333h; Further stages.;
DOI:10.1021/ol005605e

Reference yield:

: 58931-16-1,88981-35-5,110339-28-1
(R)-1-benzyloxypent-4-en-2-ol

: 264603-22-7
2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one

Guidance literature:: Multi-step reaction with 6 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

6.1: diisopropyl amine; lithium chloride; n-butyl lithium / tetrahydrofuran / 0.67 h / -98 °C

6.2: 63 percent / tetrahydrofuran / 0.33 h / -98 °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 / 6.1: Metallation / 6.2: Addition;
DOI:10.1021/ol005605e

Reference yield:

: 14618-80-5
(R)-benzyl glycidol

: 264603-22-7
2-[(4R)-5-benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl]-6-(2-hydroxy-butyl)-pyran-4-one

Guidance literature:: Multi-step reaction with 7 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

7.1: diisopropyl amine; lithium chloride; n-butyl lithium / tetrahydrofuran / 0.67 h / -98 °C

7.2: 63 percent / tetrahydrofuran / 0.33 h / -98 °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 / 7.1: Metallation / 7.2: Addition;
DOI:10.1021/ol005605e