(1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)cyclopentanol

Base Information

• Chemical Name: (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)cyclopentanol
• CAS No.: 143833-71-0
• Molecular Formula: C₂₀H₄₄O₄Si₂
• Molecular Weight: 404.738
• Mol file: 143833-71-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)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:

(-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one (26054-46-6) → (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)cyclopentanol (143833-71-0)

Guidance literature:

Multi-step reaction with 13 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

6.1: 1H-imidazole / N,N-dimethyl-formamide / 0.33 h / 20 °C / Inert atmosphere

6.2: 12 h / Inert atmosphere

7.1: dimethylaluminum chloride / dichloromethane; hexane / 3 h / 20 °C / Inert atmosphere

8.1: pyridine / 24 h / 20 °C / Inert atmosphere

9.1: sodium azide / N,N-dimethyl-formamide / 150 °C / Microwave irradiation

10.1: copper(ll) sulfate pentahydrate / methanol / 8 h / 50 °C / Sealed tube

11.1: copper(l) iodide; sodium hydroxide / methanol; water / 50 °C

12.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

12.2: Inert atmosphere

13.1: lithium aluminium tetrahydride / tetrahydrofuran / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; sodium azide; copper(ll) sulfate pentahydrate; sulfuric acid; DBN; dimethylaluminum chloride; toluene-4-sulfonic acid; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2013.03.069

Reference yield:

trityl chloride (76-83-5) + (1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)cyclopentanol (143833-71-0) → (1S,2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-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:

(1S,2R,3S,4R)-4-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-2-(2-hydroxyethyl)cyclopentanol (143833-71-0) → <1S-(1α,2β,3α,4α)>-3-(hydroxymethyl)-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane (142066-69-1)

Guidance literature:

Multi-step reaction with 7 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

6: triethylamine / CH₂Cl₂ / 0.25 h / Ambient temperature

7: 88 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature

With dmap; aluminum amalgam; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; 3 A molecular sieve; tetrabutyl ammonium fluoride; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00094a017

upstream raw materials:

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

Downstream raw materials:

<1S-(1α,2β,3α,4α)>-3-(hydroxymethyl)-2-<2-<(triphenylmethyl)oxy>ethyl>-5-oxabicyclo<2.2.1>heptane

(2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-cyclopentanol

<1S-(1α,2β,3α)>-2-<2-<(tert-butyldimethylsilyl)oxymethyl>-3-<(tert-butyldimethylsilyl)oxy>-5-methenylcyclopentanyl>ethanol triphenylmethyl ether

<1S-(1α,2β,3α,5α)>-2-<2-<<(tert-butyldimethylsilyl)oxy>methyl>-3-<(tert-butyldimethylsilyl)oxy>-5-<(methylsulfonyl)oxy>methylcyclopentanyl>ethanol triphenylmethyl ether