(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

Base Information

Chemical Name:(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one
CAS No.:1422178-91-3
Molecular Formula:C₆₀H₇₂O₉
Molecular Weight:937.226
Hs Code.:

Synonyms:(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

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Chemical Property of (1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

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Technology Process of (1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

There total 5 articles about (1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-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: 94.0%

: 1422178-90-2
(1S,5S,6R,7R,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-ol

: 1422178-91-3
(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; for 3h; Reflux;
DOI:10.1016/j.tet.2012.12.065

Reference yield:

: 37776-17-3
5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose

: 1422178-91-3
(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 °C / Inert atmosphere

1.2: 0.33 h / -78 °C / Inert atmosphere

1.3: 2 h / -78 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2012.12.065

Reference yield:

: 1422178-88-8
(1S,5S,6S,7R,9R)-5,6,9-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)octadec-3-yn-1-ol

: 1422178-91-3
(1S,5S,6S,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-one

Guidance literature:: Multi-step reaction with 3 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux

With tetrabutyl ammonium fluoride; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2012.12.065