tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane
• CAS No.: 1334297-68-5
• Molecular Formula: C₃₇H₅₁ClO₁₀Si
• Molecular Weight: 719.344
• Mol file: 1334297-68-5.mol

Synonyms:tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane

Chemical Property of tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane

There total 4 articles about tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane 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: 98.0%

(2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (866605-97-2) + chloromethyl methyl ether (107-30-2) → tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane (1334297-68-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2014.04.036

Reference yield:

(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (866605-96-1) → tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane (1334297-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

2: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C

With triethylsilane; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.bmc.2014.04.036

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → tert-butyl(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(methoxymethoxy)-6-((methoxymethoxy)methyl)tetrahydro-2H-pyran-2-yl)benzyloxy)diphenylsilane (1334297-68-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tert.-butyl lithium / tetrahydrofuran / 5 h / -78 °C

1.2: -78 - 20 °C

2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C

3.1: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 24 h / 20 °C

With triethylsilane; boron trifluoride diethyl etherate; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2014.04.036

upstream raw materials:

(3R,4S,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

chloromethyl methyl ether

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

Downstream raw materials:

1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-3-ethylimidazolidine-2,4-dione

1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-3-tritylimidazolidine-2,4-dione

1-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-3-isopropylimidazolidine-2,4-dione

3-(4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-1-methylimidazolidine-2,4-dione