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

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Chemical Name:(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane
CAS No.:1259018-13-7
Molecular Formula:C₅₀H₆₁ClO₆Si
Molecular Weight:821.569
Hs Code.:

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

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

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Technology Process of (2-chloro-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-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:

: 1260241-94-8
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)tetrahydro-2H-pyran-2-ol

: 1259018-13-7
(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Guidance literature:: (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-2-(4-chloro-3-((triisopropylsilyloxy)methyl)phenyl)tetrahydro-2H-pyran-2-ol; With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -50 - -10 ℃; Inert atmosphere;

With water; potassium carbonate; In dichloromethane; at -10 ℃;

Reference yield:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 1225430-36-3
(5-bromo-2-chlorobenzyloxy)triisopropylsilane

: 1259018-13-7
(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Guidance literature:: (5-bromo-2-chlorobenzyloxy)triisopropylsilane; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; Inert atmosphere;

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one; In tetrahydrofuran; hexane; at -78 ℃; Further stages; Inert atmosphere;
DOI:10.1016/j.bmc.2010.01.073

Reference yield:

: 21739-92-4
5-bromo-2-chlorobenzoic acid

: 1259018-13-7
(2-chloro-5-((3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzyloxy)triisopropylsilane

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane dimethyl sulfide complex / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

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

3.1: n-butyllithium / tetrahydrofuran; hexanes / 1.5 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / -50 - -10 °C / Inert atmosphere

With 1H-imidazole; triethylsilane; dmap; n-butyllithium; borane dimethyl sulfide complex; boron trifluoride diethyl etherate; In tetrahydrofuran; hexanes; dichloromethane; N,N-dimethyl-formamide;