(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

Base Information

Chemical Name:(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one
CAS No.:1352746-52-1
Molecular Formula:C₅₀H₉₄O₇Si₄
Molecular Weight:919.634
Hs Code.:

(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

Synonyms:(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

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Chemical Property of (3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

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Technology Process of (3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

There total 16 articles about (3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one 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: 64.0%

: 1352746-51-0
(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

: (4R)-4,5-bis-(tert-butyldimethylsilyloxy)-2-(trimethylsilyl-methyl)pent-1-ene

: 1352746-52-1
(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

Guidance literature:: With zinc(II) iodide; In dichloromethane; at 20 ℃; for 48h; stereoselective reaction; Molecular sieve; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

: 1352746-52-1
(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

Guidance literature:: Multi-step reaction with 8 steps

1: lithium tri-t-butoxyaluminum hydride; lithium iodide / tetrahydrofuran; diethyl ether / 18 h / -78 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

4: 1H-imidazole / dichloromethane / 0 °C

5: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

7: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

8: zinc(II) iodide / dichloromethane / 48 h / 20 °C / Molecular sieve; Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; zinc(II) iodide; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 1352746-56-5
(2R)-1-tert-butyldimethylsilyloxy-4-(trimethylsilylmethyl)-pent-4-en-2-ol

: 1352746-52-1
(3S,5R,7S,15R,10E)-7-benzyloxy-1,15,16-tris-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

2: zinc(II) iodide / dichloromethane / 48 h / 20 °C / Molecular sieve; Inert atmosphere

With triethylamine; zinc(II) iodide; In dichloromethane;
DOI:10.1016/j.tet.2011.09.064