(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

Base Information

• Chemical Name: (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
• CAS No.: 220772-80-5
• Molecular Formula: C₅₁H₇₆O₁₅S₂
• Molecular Weight: 993.287
• Mol file: 220772-80-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 36 articles about (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 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: 87.0%

methanesulfonyl chloride (124-63-0) + (2R,3S,4S,5S,6S,9S,10S,13R,14S)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane-3,4-diol (220772-79-2) → (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 (220772-80-5)

Guidance literature:

With triethylamine; In dichloromethane; 0 deg C to RT;

DOI:10.1016/S0040-4039(98)02439-3

Reference yield:

2,5-anhydro-D-mannitol (41107-82-8) → (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 (220772-80-5)

Guidance literature:

Multi-step reaction with 14 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

13.1: 47.8 mg / tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / 20 °C

14.1: triethylamine / CH₂Cl₂ / 12 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; tetrabutyl ammonium fluoride; hydrogen; 4-methylmorpholine N-oxide; triethylamine; 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:

n-decyl magnesium bromide (17049-50-2) → (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 (220772-80-5)

Guidance literature:

Multi-step reaction with 17 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

16.1: 47.8 mg / tetrabutylammonium fluoride / tetrahydrofuran / 5.5 h / 20 °C

17.1: triethylamine / CH₂Cl₂ / 12 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; triethylamine; 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

upstream raw materials:

methanesulfonyl chloride

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

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

n-decyl magnesium bromide

Downstream raw materials:

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

(2S,5S,6S,9S,10S,13R,14S)-2,5:10,14-dioxido-6,9,13-tris(methoxymethoxy)-1-trityloxytetracos-3-ene