(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

Base Information

Chemical Name:(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol
CAS No.:1422178-85-5
Molecular Formula:C₅₀H₅₄O₉
Molecular Weight:798.973
Hs Code.:

Synonyms:(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

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Chemical Property of (2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

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Technology Process of (2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

There total 4 articles about (2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-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: 76.0%

: 1422178-84-4
tert-butyldimethyl(((2R,3S,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-yl)oxy)silane

: 1422178-85-5
(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;
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

: 1422178-85-5
(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

Guidance literature:: Multi-step reaction with 3 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 / 6 h / 0 - 20 °C

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

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2012.12.065

Reference yield:

: 1319725-94-4
tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-yn-2-yloxy)silane

: 1422178-85-5
(2R,3R,4S,8S)-1,3,4,8-tetrakis(benzyloxy)-8-((3aR,5R,6-S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)oct-5-yn-2-ol

Guidance literature:: Multi-step reaction with 3 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 / 6 h / 0 - 20 °C

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

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2012.12.065