[(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol

Base Information

• Chemical Name: [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol
• CAS No.: 339291-65-5
• Molecular Formula: C₂₆H₄₄O₄Si
• Molecular Weight: 448.718

Synonyms:[(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol

Chemical Property of [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol

Chemical Property:

Purity/Quality:

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Technology Process of [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol

There total 7 articles about [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol 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:

4-methoxybenzaldehyde diethylacetal (2403-58-9) → [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol (339291-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

With dmap; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1021/jo005683f

Reference yield:

((2R,3R)-3-Hydroxy-2-hydroxymethyl-1-methyl-cyclopentyl)-acetic acid methyl ester → [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol (339291-65-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

2.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

3.1: DMSO; oxalyl chloride; Et₃N

4.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

4.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

5.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

6.1: 73 percent / DMAP / dimethylformamide / 20 °C

With dmap; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Swern oxidation;

DOI:10.1021/jo005683f

Reference yield:

cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2,5-dimethyl-, ethyl ester, (2S,4aR,5RS,7aR) → [(1R,2S,5R)-2-[(Z)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-but-2-enyl]-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-methanol (339291-65-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: p-TsOH / methanol / 13 h / Heating

2.1: 26.5 g / dimethylformamide / 3 h / 50 °C / 10 - 15 Torr

3.1: 83 percent / DIBAL / CH₂Cl₂; cyclohexane / 5 h / -78 °C

4.1: DMSO; oxalyl chloride; Et₃N

5.1: 18-crown-6/acetonitrile complex; KHMDS / tetrahydrofuran / 0.5 h / -78 °C

5.2: 1.788 g / tetrahydrofuran / 1 h / -78 °C

6.1: 97 percent / DIBAL / hexane; CH₂Cl₂ / -78 - 20 °C

7.1: 73 percent / DMAP / dimethylformamide / 20 °C

With dmap; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; acetonitrile; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 4.1: Swern oxidation;

DOI:10.1021/jo005683f

upstream raw materials:

4-methoxybenzaldehyde diethylacetal

2-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-ethanol

cyclopenta-1,3-dioxin-5-acetic acid, hexahydro-2-(p-methoxybenzylidene)-5-methyl, methyl ester, (2S,4R,5S,7R)

(Z)-4-[(2S,4aR,5S,7aR)-2-(4-Methoxy-phenyl)-5-methyl-hexahydro-cyclopenta[1,3]dioxin-5-yl]-2-methyl-but-2-enoic acid ethyl ester

Downstream raw materials:

(2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienal

(2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dien-1-ol

(2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Chloro-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

(2E,4E)-5-[(1S,2S,5R)-2-((Z)-4-Hydroxy-3-methyl-but-2-enyl)-5-(4-methoxy-benzyloxy)-2-methyl-cyclopentyl]-penta-2,4-dienoic acid methyl ester

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