(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

Base Information

Chemical Name:(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane
CAS No.:1338566-07-6
Molecular Formula:C₃₁H₄₆O₄S₂Si
Molecular Weight:574.921
Hs Code.:

Synonyms:(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

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Chemical Property of (((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

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Technology Process of (((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

There total 5 articles about (((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane 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: 48.0%

: 505-23-7
1,3 dithiane

: 1338566-06-5
((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate

: 1338566-07-6
(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

Guidance literature:: 1,3 dithiane; With n-butyllithium; In tetrahydrofuran; hexane; at -20 ℃; for 1.5h; Inert atmosphere;

((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; at -20 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol202467z

Reference yield: 48.0%

: 505-23-7
1,3 dithiane

: 436153-70-7
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

: 1338566-07-6
(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

Guidance literature:: With n-butyllithium; In tetrahydrofuran; Inert atmosphere;
DOI:10.1021/jo302267f

Reference yield:

: 632354-40-6
(2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-hydroxymethyltetrahydropyran-3-ol

: 1338566-07-6
(((2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-yl)oxy)-t-butyldimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -80 °C

1.2: 1.25 h / -80 - 45 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -20 °C / Inert atmosphere

2.2: 1 h / -20 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol202467z