(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

Base Information

Chemical Name:(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
CAS No.:1422178-88-8
Molecular Formula:C₅₉H₈₂O₉Si
Molecular Weight:963.38
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 1 articles about (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 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: 82.0%

: 1319725-92-2
C₄₃H₆₂O₄Si

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

: 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

Guidance literature:: C₄₃H₆₂O₄Si; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

With boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h; Inert atmosphere;

5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tet.2012.12.065

Reference yield: 82.0%

: 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

: 100-39-0
benzyl bromide

: 1422178-89-9
tert-butyldimethyl(((1S,5S,6S,7R,9R)-1,5,6,9-tetrakis(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)octadec-3-yn-7-yl)oxy)silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃;
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

: 1422178-90-2
(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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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