(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

Base Information

Chemical Name:(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
CAS No.:454474-68-1
Molecular Formula:C₆₁H₁₀₀O₁₁Si₂
Molecular Weight:1065.63
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 33 articles about (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 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:

: 17049-50-2
n-decyl magnesium bromide

: 454474-68-1
(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

Guidance literature:: Multi-step reaction with 15 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

14.1: Zn(BH₄)2 / diethyl ether / -10 °C

15.1: N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; triethylsilane; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; 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:

: 41107-82-8
2,5-anhydro-D-mannitol

: 454474-68-1
(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

Guidance literature:: Multi-step reaction with 12 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

11.1: Zn(BH₄)2 / diethyl ether / -10 °C

12.1: N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / 0 - 20 °C

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; 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:

: 48229-09-0
2,3,4-tri-O-benzyl-D-galactopyranose

: 454474-68-1
(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

Guidance literature:: Multi-step reaction with 17 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

16.1: Zn(BH₄)2 / diethyl ether / -10 °C

17.1: N,N-diisopropylethylamine / CH₂Cl₂ / 18 h / 0 - 20 °C

With 1H-imidazole; triethylsilane; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; 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