(2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Base Information

• Chemical Name: (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane
• CAS No.: 1313512-92-3
• Molecular Formula: C₅₁H₆₃ClO₇Si
• Molecular Weight: 851.596

Synonyms:(2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Chemical Property of (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

There total 6 articles about (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane 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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) + (5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane (1259020-50-2) → (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane (1313512-92-3)

Guidance literature:

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -50 - -10 ℃; Inert atmosphere;

DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

5-bromo-2-chloro-4-hydroxybenzonitrile (1259020-46-6) → (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane (1313512-92-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hydroxide monohydrate / tetrahydrofuran / 15 h / 75 °C / Inert atmosphere

2.1: sodium hydroxide / ethanol; water / 9 h / 100 °C / Inert atmosphere

2.2: 0 °C

3.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 75 °C / Inert atmosphere

4.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

5.2: 1.5 h / -78 °C / Inert atmosphere

5.3: -50 - -10 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; lithium hydroxide monohydrate; dimethylsulfide borane complex; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2011.03.052

Reference yield:

5-bromo-2-chloro-4-methoxybenzonitrile (1259020-79-5) → (2-chloro-4-methoxy-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane (1313512-92-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / ethanol; water / 9 h / 100 °C / Inert atmosphere

1.2: 0 °C

2.1: dimethylsulfide borane complex / tetrahydrofuran / 0 - 75 °C / Inert atmosphere

3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 15 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

4.2: 1.5 h / -78 °C / Inert atmosphere

4.3: -50 - -10 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; dimethylsulfide borane complex; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.ejmech.2011.03.052

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

(5-bromo-2-chloro-4-methoxybenzyloxy)triisopropylsilane

triisopropylsilyl chloride

(5-bromo-2-chloro-4-methoxyphenyl)methanol

Downstream raw materials:

(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(4-fluorophenyl)thiazol-2-yl)methyl)-2-methoxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4R,5S,6R)-2-(4-chloro-2-methoxy-5-((5-phenylthiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4R,5S,6R)-2-(4-chloro-2-methoxy-5-((5-(thiophen-3-yl)thiazol-2-yl)methyl)phenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4R,5S,6R)-2-(4-chloro-5-((5-(thiophen-2-yl)thiazol-2-yl)methyl)-2-methoxyphenyl)-6-(hydroxymethyl)-tetrahydro-2H-pyran-3,4,5-triol

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