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

Base Information

Chemical Name:(1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol
CAS No.:1422178-83-3
Molecular Formula:C₄₉H₆₂O₉Si
Molecular Weight:823.111
Hs Code.:

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

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

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Chemical Property of (1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol

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Technology Process of (1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol

There total 1 articles about (1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-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: 79.0%

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

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

: 1422178-83-3
(1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol

Guidance literature:: tert-butyldimethyl((2R,3S,4S)-1,3,4-tris(benzyloxy)hex-5-yn-2-yloxy)silane; 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: 81.0%

: 1422178-83-3
(1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol

: 100-39-0
benzyl bromide

: 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

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; for 6h;
DOI:10.1016/j.tet.2012.12.065

Reference yield:

: 1422178-83-3
(1S,5S,6S,7R)-5,6,8-tris(benzyloxy)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)oct-3-yn-1-ol

: 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 2 steps

1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 6 h / 0 - 20 °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