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

Base Information

• Chemical Name: (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-cyclopentanol
• CAS No.: 142066-61-3
• Molecular Formula: C₄₀H₆₀O₄Si₂
• Molecular Weight: 661.085
• Mol file: 142066-61-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-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-(1α,2β,3α,5α,β)>-2-<2-<(tert-butyldimethylsilyloxy)methyl>-3-<(tert-butyldimethylsilyl)oxy>-5-hydroxy-5-<(N-methyl-S-phenylsulfonimidoyl)methyl>cyclopentanyl>ethanol triphenylmethyl ether → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-cyclopentanol (142066-61-3) + <1S-(1α,2β,3α)>-2-<2-<(tert-butyldimethylsilyl)oxymethyl>-3-<(tert-butyldimethylsilyl)oxy>-5-methenylcyclopentanyl>ethanol triphenylmethyl ether (142066-59-9)

Guidance literature:

With aluminum amalgam; acetic acid; In tetrahydrofuran; at 20 - 30 ℃; for 1h; Title compound not separated from byproducts;

DOI:10.1021/jm00094a017

Reference yield:

trityl chloride (76-83-5) → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-cyclopentanol (142066-61-3)

Guidance literature:

Multi-step reaction with 4 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

With dmap; aluminum amalgam; dipyridinium dichromate; 3 A molecular sieve; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00094a017

Reference yield:

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one (117624-93-8) → (2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-2-(2-trityloxy-ethyl)-cyclopentanol (142066-61-3)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium borohydride / methanol; H₂O / 6 h / Ambient temperature

2: 4-(dimethylamino)pyridine, triethylamine / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

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

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

5: 50percent aq. AcOH, Al(Hg) / tetrahydrofuran / 1 h / 20 - 30 °C

With dmap; sodium tetrahydroborate; aluminum amalgam; dipyridinium dichromate; 3 A molecular sieve; methylmagnesium chloride; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00094a017

upstream raw materials:

trityl chloride

(1S,5R,6R,7R)-6-<<(tert-butyldimethylsilyl)oxy>methyl>-7-<(tert-butyldimethylsilyl)oxy>-2-oxabicyclo<3.3.0>octane-3-one

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

Refernces