(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

Base Information

Chemical Name:(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran
CAS No.:454474-62-5
Molecular Formula:C₁₆H₃₂O₅
Molecular Weight:304.427
Hs Code.:

Synonyms:(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

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Chemical Property of (2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

Chemical Property:

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Technology Process of (2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

There total 1 articles about (2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran 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: 52.0%

: 454474-61-4
(2R,3R,4S,5R,6S)-3,4,5-tribenzyloxy-2-(1-tert-butyldiphenylsilyloxymethyl)-6-decyltetrahydropyran

: 454474-62-5
(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

: 220772-65-6
(2R,3R,4S,5R,6S)-2-(1-tert-butyldiphenylsilyl)oxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

Guidance literature:: With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; at 20 ℃; for 48h;
DOI:10.1021/jo020211h

Reference yield:

: 454474-62-5
(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

: 220772-80-5
(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

Guidance literature:: Multi-step reaction with 14 steps

1.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

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

2.2: 66 percent / 7 h / 130 °C

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

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

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

6.1: 3.64 g / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

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

7.2: 100 percent / triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °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 1H-imidazole; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; Dowex 50W X-8 (H⁽¹⁺⁾) resin; (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

Reference yield:

: 454474-62-5
(2R,3R,4S,5R,6S)-2-hydroxymethyl-3,4,5-trihydroxy-6-decyltetrahydropyran

: 220772-77-0
(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

Guidance literature:: Multi-step reaction with 11 steps

1.1: 10.4 g / imidazole / dimethylformamide / 18 h / 20 °C

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

2.2: 66 percent / 7 h / 130 °C

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

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

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

6.1: 3.64 g / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

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

7.2: 100 percent / triethylamine / CH₂Cl₂; dimethylsulfoxide / -70 - 0 °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

With 1H-imidazole; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; zinc(II) tetrahydroborate; oxalyl dichloride; 4 A molecular sieve; Dowex 50W X-8 (H⁽¹⁺⁾) resin; (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