(2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

Base Information

• Chemical Name: (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one
• CAS No.: 454474-67-0
• Molecular Formula: C₅₉H₉₄O₁₀Si₂
• Molecular Weight: 1019.56
• Mol file: 454474-67-0.mol

Synonyms:(2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

Chemical Property of (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one

There total 31 articles about (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one 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:

n-decyl magnesium bromide (17049-50-2) → (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one (454474-67-0)

Guidance literature:

Multi-step reaction with 13 steps

1.1: diethyl ether / 2.5 h / -78 °C

2.1: 1.17 g / triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -40 - -30 °C

3.1: hydrogen / 10percent Pd/C / methanol; ethyl acetate / 96 h / 20 °C

4.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

5.1: trimethyl orthoformate; d-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

5.2: 66 percent / 7 h / 130 °C

6.1: hydrogen / 10percent Pd/C / ethyl acetate; methanol / 8 h / 20 °C

7.1: sodium methoxide; Dowex 50W X-8 (H⁽¹⁺⁾) resin / methanol; CH₂Cl₂ / 96 h / 20 °C

8.1: N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / 0 - 20 °C

9.1: 3.64 g / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

10.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -70 °C

10.2: 100 percent / triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °C

11.1: 78 percent / n-BuLi; anhydrous cerium chloride / tetrahydrofuran; hexane / 5 h / -78 - -23 °C

12.1: hydrogen / PtO₂ / ethyl acetate / 7 h / 20 °C

13.1: 44.5 mg / n-tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.2 h / 20 °C

With 1H-imidazole; triethylsilane; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; Dowex 50W X-8 (H⁽¹⁺⁾) resin; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; trimethyl orthoformate; platinum(IV) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

Reference yield:

2,5-anhydro-D-mannitol (41107-82-8) → (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one (454474-67-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 69 percent / pyridine / 19 h / 0 - 20 °C

2.1: 387 mg / imidazole / dimethylformamide / 18 h / 20 °C

3.1: 71 percent / lithium aluminium hydride / diethyl ether / 1 h / 0 °C

4.1: 68 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 6 h / -10 - 0 °C

5.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 1 h / -70 °C

5.2: triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °C

6.1: 65 percent / ZnCl₂ / CH₂Cl₂; diethyl ether; tetrahydrofuran / 18 h / -70 - 20 °C

7.1: 90 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 78 percent / n-BuLi; anhydrous cerium chloride / tetrahydrofuran; hexane / 5 h / -78 - -23 °C

9.1: hydrogen / PtO₂ / ethyl acetate / 7 h / 20 °C

10.1: 44.5 mg / n-tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.2 h / 20 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; hydrogen; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

Reference yield:

2,3,4-tri-O-benzyl-D-galactopyranose (48229-09-0) → (2R,3R,4R,5R,6S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-one (454474-67-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 89 percent / imidazole / dimethylformamide / 28 h / 20 °C

2.1: oxalyl chloride / dimethylsulfoxide; CH₂Cl₂ / 0.5 h / -70 °C

2.2: triethylamine / dimethylsulfoxide; CH₂Cl₂ / -70 - 0 °C

3.1: diethyl ether / 2 h / -78 °C

4.1: 7.71 g / triethylsilane; BF₃*Et₂O / CH₂Cl₂ / 3.5 h / -20 °C

5.1: 36 percent / H₂ / Pd/C / methanol; ethyl acetate / 48 h / 20 °C

6.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

7.1: trimethyl orthoformate; d-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

7.2: 66 percent / 7 h / 130 °C

8.1: hydrogen / 10percent Pd/C / ethyl acetate; methanol / 8 h / 20 °C

9.1: sodium methoxide; Dowex 50W X-8 (H⁽¹⁺⁾) resin / methanol; CH₂Cl₂ / 96 h / 20 °C

10.1: N,N-diisopropylethylamine / CH₂Cl₂ / 48 h / 0 - 20 °C

11.1: 3.64 g / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

12.1: oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -70 °C

12.2: 100 percent / triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °C

13.1: 78 percent / n-BuLi; anhydrous cerium chloride / tetrahydrofuran; hexane / 5 h / -78 - -23 °C

14.1: hydrogen / PtO₂ / ethyl acetate / 7 h / 20 °C

15.1: 44.5 mg / n-tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1.2 h / 20 °C

With 1H-imidazole; triethylsilane; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; Dowex 50W X-8 (H⁽¹⁺⁾) resin; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; trimethyl orthoformate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

upstream raw materials:

(S)-4-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-trityloxymethyl-tetrahydro-furan-2-yl]-1-((2S,5R,6S)-6-decyl-5-methoxymethoxy-tetrahydro-pyran-2-yl)-4-methoxymethoxy-butan-1-ol

2,3,4-tri-O-benzyl-D-galactopyranose

n-decyl magnesium bromide

trityl chloride

Downstream raw materials:

(2R,3R,4R,5R,6S,9S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracosan-9-ol

(2R,3R,4R,5R,6S,9S,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane

(2R,3R,4R,5R,6S,9S,10S,13R,14S)-2,5:10,14-dioxido-3,4-bis(methanesulfonyloxy)-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane

(2R,3S,4S,5S,6S,9S,10S,13R,14S)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane-3,4-diol