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

Base Information

• Chemical Name: (2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 866605-97-2
• Molecular Formula: C₂₉H₃₅ClO₆Si
• Molecular Weight: 543.132
• Mol file: 866605-97-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

(5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane (866605-95-0) → (2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (866605-97-2)

Guidance literature:

Multi-step reaction with 2 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

With triethylsilane; boron trifluoride diethyl etherate; tert.-butyl lithium; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2014.04.036

Reference yield:

(5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane (866605-95-0) + (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) → (2S,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (866605-97-2) + (2R,3R,4R,5S,6R)-2-(3-((tert-butyldiphenylsilyloxy)methyl)-4-chlorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Guidance literature:

Multi-step reaction with 2 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

With triethylsilane; boron trifluoride diethyl etherate; tert.-butyl lithium; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.bmc.2014.04.036

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

upstream raw materials:

(5-bromo-2-chlorobenzyloxy)(tert-butyl)diphenylsilane

(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