(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

Base Information

Chemical Name:(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol
CAS No.:149585-89-7
Molecular Formula:C₁₉H₃₈O₅Si
Molecular Weight:374.593
Hs Code.:

Synonyms:(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

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Chemical Property of (1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

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Technology Process of (1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

There total 1 articles about (1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol 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:

: 26054-46-6
(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one

: 149585-89-7
(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: sulfuric acid / 24 h / 50 - 80 °C / Sealed tube

2.1: DBN / methanol / 12 h / 20 °C

3.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

3.2: 8 h / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; lithium aluminium tetrahydride; sulfuric acid; DBN; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

: 76-83-5
trityl chloride

: 149585-89-7
(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

: (1S,2R,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tetrahydro-pyran-2-yloxy)-2-(2-trityloxy-ethyl)-cyclopentanol

Guidance literature:: With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 ℃; for 1h;
DOI:10.1021/jm00094a017

Reference yield:

: 149585-89-7
(1S,2R,3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)-4-(tetrahydro-2H-pyran-2-yloxy)cyclopentanol

: [(1S,2S,3S,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(tetrahydro-pyran-2-yloxy)-2-(2-trityloxy-ethyl)-cyclopentyl]-methanol

Guidance literature:: Multi-step reaction with 5 steps

1: 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

2: 3A-molecular sieves, pyridinium dichromate / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) MeMgCl / 1.) THF, from 0 deg C to 5 deg C, 15 min, 2.) THF, -78 deg C, 15 min

4: 50percent aq. AcOH, Al(Hg) / tetrahydrofuran / 1 h / 20 - 30 °C

5: 9-borabicyclo<3.3.1>nonane (9-BBN) / tetrahydrofuran / 4 h / 0 - 5 °C

With dmap; aluminum amalgam; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; 3 A molecular sieve; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00094a017