(E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester
• CAS No.: 635727-27-4
• Molecular Formula: C₂₆H₃₄O₆
• Molecular Weight: 442.552
• Mol file: 635727-27-4.mol

Synonyms:(E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester

Chemical Property of (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester

There total 6 articles about (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester 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:

(2R,3S)-1-Benzyloxy-3-methyl-pent-4-en-2-ol (635727-09-2) → (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester (635727-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / NaH; n-Bu₄NI / tetrahydrofuran / 9 h / 20 °C

2.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 4 h / 20 °C

3.1: diethyl ether / 5 h / -78 °C

3.2: 1.7 g / aq. NaOH; H₂O₂ / 6 h

4.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 6 h / 20 °C

5.1: 812 mg / benzene / 3 h / 80 - 90 °C

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; benzene; 5.1: Wittig reaction;

DOI:10.1055/s-2004-822340

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester (635727-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 97 percent / NaH; n-Bu₄NI / tetrahydrofuran / 9 h / 20 °C

2.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 4 h / 20 °C

3.1: diethyl ether / 5 h / -78 °C

3.2: 1.7 g / aq. NaOH; H₂O₂ / 6 h

4.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 6 h / 20 °C

5.1: 812 mg / benzene / 3 h / 80 - 90 °C

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; diethyl ether; benzene; 5.1: Wittig reaction;

DOI:10.1055/s-2004-822340

Reference yield:

(2R,3R)-4-Benzyloxy-3-(4-methoxy-benzyloxy)-2-methyl-butyraldehyde → (E)-(5R,6S,7R)-8-Benzyloxy-5-hydroxy-7-(4-methoxy-benzyloxy)-6-methyl-oct-2-enoic acid ethyl ester (635727-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethyl ether / 5 h / -78 °C

1.2: 1.7 g / aq. NaOH; H₂O₂ / 6 h

2.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 6 h / 20 °C

3.1: 812 mg / benzene / 3 h / 80 - 90 °C

With sodium periodate; osmium(VIII) oxide; In tetrahydrofuran; diethyl ether; benzene; 3.1: Wittig reaction;

DOI:10.1055/s-2004-822340

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

(2R,3S)-1-Benzyloxy-3-methyl-pent-4-en-2-ol

p-methoxybenzyl chloride

1-{[(2R,3S)-1-(benzyloxy)-3-methylpent-4-en-2-yloxy]methyl}-4-methoxy-benzene

Downstream raw materials:

ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

ethyl (5R,6R,7R)-8-benzyloxy-7-hydroxy-6-methyl-5-triisopropylsilanyloxy-(2E)-octenoate

(E)-4-((2R,4R,5R,6R)-6-Benzyloxymethyl-5-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-2-enoic acid ethyl ester