tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane
• CAS No.: 516457-54-8
• Molecular Formula: C₃₀H₄₉ClO₆Si
• Molecular Weight: 569.254

Synonyms:tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane

There total 18 articles about tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane 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: 45.0%

2-{(E)-6-[(2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-2-yl]-4-trimethylsilanyl-hex-3-enyloxy}-tetrahydro-pyran → tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane (516457-54-8)

Guidance literature:

With N-chloro-succinimide; water; In N,N-dimethyl-formamide; at 50 ℃; for 6h;

DOI:10.1021/ol0341804

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane (516457-54-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 93 percent / p-TsOH

2.1: 74 percent / n-BuLi / diethyl ether; hexane

3.1: DIBAL / diethyl ether; hexane

3.2: pyridine / diethyl ether

3.3: 91 percent / Br₂ / CH₂Cl₂

4.1: 99 percent / Br₂ / pyridine; CH₂Cl₂ / Irradiation

5.1: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide

6.1: 45 percent / H₂O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C

With N-chloro-succinimide; n-butyllithium; water; bromine; sec.-butyllithium; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0341804

Reference yield:

2-(but-3-yn-1-yloxy)tetrahydropyran (40365-61-5) → tert-Butyl-[(2S,3S,5S)-5-[(Z)-3-chloro-6-(tetrahydro-pyran-2-yloxy)-hex-3-enyl]-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane (516457-54-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 74 percent / n-BuLi / diethyl ether; hexane

2.1: DIBAL / diethyl ether; hexane

2.2: pyridine / diethyl ether

2.3: 91 percent / Br₂ / CH₂Cl₂

3.1: 99 percent / Br₂ / pyridine; CH₂Cl₂ / Irradiation

4.1: 68 percent / s-BuLi / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide

5.1: 45 percent / H₂O; N-chlorosuccinimide / dimethylformamide / 6 h / 50 °C

With N-chloro-succinimide; n-butyllithium; water; bromine; sec.-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0341804

upstream raw materials:

3,4-dihydro-2H-pyran

2-(but-3-yn-1-yloxy)tetrahydropyran

trimethyl(4-((tetrahydro-2H-pyran-2-yl)oxy)but-1-yn-1-yl)silane

(2S,3S)-4-(p-methoxybenzyloxy)-2,3-(isopropylidenedioxy)-butan-1-ol

Downstream raw materials:

C₅₀H₆₃ClO₇Si₂

tert-Butyl-[(2S,3S,5S)-5-{(3Z,6Z)-3-chloro-8-[(4-methoxy-phenyl)-diphenyl-methoxy]-7-methyl-octa-3,6-dienyl}-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yloxy]-dimethyl-silane

Bromo-acetic acid (2S,3S,5S)-5-{(3Z,6Z)-3-chloro-8-[(4-methoxy-phenyl)-diphenyl-methoxy]-7-methyl-octa-3,6-dienyl}-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-yl ester

(2S,3S,5S)-5-{(3Z,6Z)-3-Chloro-8-[(4-methoxy-phenyl)-diphenyl-methoxy]-7-methyl-octa-3,6-dienyl}-2-(4-methoxy-benzyloxymethyl)-tetrahydro-furan-3-ol

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