1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

Base Information

Chemical Name:1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose
CAS No.:1385068-65-4
Molecular Formula:C₄₃H₄₄O₁₀Si
Molecular Weight:748.902
Hs Code.:

Synonyms:1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

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Chemical Property of 1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

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Technology Process of 1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

There total 4 articles about 1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose 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:

: C₁₅H₂₈O₆Si

: 98-88-4
benzoyl chloride

: 1385068-65-4
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

: 1385068-61-0
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-α-D-glucopyranose

Guidance literature:: With pyridine; dmap; at 20 ℃; for 13h; optical yield given as %de;
DOI:10.1016/j.tetlet.2012.05.111

Reference yield:

: 1385068-26-7
1,2,5,6-bis-O-isopropylidene-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-α-D-glucofuranose

: 1385068-65-4
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

: 1385068-61-0
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 2 steps

1: water; trifluoroacetic acid / tetrahydrofuran / 5 h / 60 °C

2: pyridine; dmap / 13 h / 20 °C

With pyridine; dmap; water; trifluoroacetic acid; In tetrahydrofuran;
DOI:10.1016/j.tetlet.2012.05.111

Reference yield:

: 67441-18-3
(3aR,4S,5R,6aR)-5-(2,2-dimethyl-[1,3]dioxolan-4R-yl)-2,2-dimethyl-6-prop-2-ynyloxy-tetrahydrofuro[2,3-d][1,3]dioxole

: 1385068-65-4
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-β-D-glucopyranose

: 1385068-61-0
1,2,4,6-tetra-O-benzoyl-3-O-(3-tert-butyldimethylsilylprop-2-yn-1-yl)-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -78 °C

1.2: 1 h / 0 °C

2.1: water; trifluoroacetic acid / tetrahydrofuran / 5 h / 60 °C

3.1: pyridine; dmap / 13 h / 20 °C

With pyridine; dmap; n-butyllithium; water; trifluoroacetic acid; In tetrahydrofuran; hexane;
DOI:10.1016/j.tetlet.2012.05.111