(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

Base Information

Chemical Name:(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol
CAS No.:1374433-35-8
Molecular Formula:C₂₉H₅₀O₅Si
Molecular Weight:506.798
Hs Code.:

Synonyms:(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

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Chemical Property of (2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

Chemical Property:

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Technology Process of (2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

There total 9 articles about (2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol 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:

: 1374433-32-5
(2S,15S,E)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-13-en-11-yn-2-ol

: (2S,13S,14R,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

: 1374433-35-8
(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

Guidance literature:: With methanesulfonamide; AD-mix β; In water; tert-butyl alcohol; at 0 ℃; for 72h; optical yield given as %de;
DOI:10.1002/ejoc.201101673

Reference yield:

: 1374433-14-3
(S)-dodec-11-yn-2-ol

: (2S,13S,14R,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

: 1374433-35-8
(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

Guidance literature:: Multi-step reaction with 2 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / 0 °C

1.2: 2.67 h / 0 - 20 °C

2.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C

With bis-triphenylphosphine-palladium(II) chloride; methanesulfonamide; AD-mix β; triethylamine; In water; tert-butyl alcohol; 1.1: Sonogashira coupling / 1.2: Sonogashira coupling / 2.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201101673

Reference yield:

: 1374433-25-6
(4R,5S)-4-(benzyloxymethyl)-5-(chloromethyl)-2,2-dimethyl-1,3-di-oxolane

: (2S,13S,14R,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

: 1374433-35-8
(2S,13R,14S,15R)-16-(benzyloxy)-15-(tert-butyldimethylsilyloxy)hexadec-11-yne-2,13,14-triol

Guidance literature:: Multi-step reaction with 5 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 1 h / -30 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 0 - 20 °C

3.1: zirconocene dichloride; lithium triethylborohydride / tetrahydrofuran / 0.5 h / 20 °C

3.2: 0.5 h / 0 °C

4.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine / 0.25 h / 0 °C

4.2: 2.67 h / 0 - 20 °C

5.1: AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; zirconocene dichloride; methanesulfonamide; AD-mix β; lithium triethylborohydride; triethylamine; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Sonogashira coupling / 4.2: Sonogashira coupling / 5.1: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201101673