(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

Base Information

• Chemical Name: (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
• CAS No.: 454475-02-6
• Molecular Formula: C₅₉H₉₆O₁₀Si₂
• Molecular Weight: 1021.58
• Mol file: 454475-02-6.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 30 articles about (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 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:

(2R,3R,4R,5R,6S,9RS,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracos-7-yn-9-ol (220772-76-9) → (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 (454475-02-6)

Guidance literature:

With hydrogen; platinum(IV) oxide; In ethyl acetate; at 20 ℃; for 7h;

DOI:10.1021/jo020211h

Reference yield:

n-decyl magnesium bromide (17049-50-2) → (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 (454475-02-6)

Guidance literature:

Multi-step reaction with 12 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

With 1H-imidazole; triethylsilane; n-butyllithium; cerium(III) chloride; oxalyl dichloride; Dowex 50W X-8 (H⁽¹⁺⁾) resin; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; 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) → (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 (454475-02-6)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; cerium(III) chloride; oxalyl dichloride; hydrogen; 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

upstream raw materials:

(2R,3R,4R,5R,6S,9RS,10S,13R,14S)-3,4-bis(tert-butyldimethylsilyloxy)-2,5:10,14-dioxido-6,13-bis(methoxymethoxy)-1-trityloxytetracos-7-yn-9-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-6,9,13-tris(methoxymethoxy)-1-trityloxytetracosane

(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)-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