(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

Base Information

Chemical Name:(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol
CAS No.:944415-98-9
Molecular Formula:C₂₇H₃₄O₅
Molecular Weight:438.564
Hs Code.:

Synonyms:(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

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Chemical Property of (2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

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Technology Process of (2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

There total 4 articles about (2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-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: 96.0%

: 934165-89-6
((S)-2-methyl-but-3-ynyloxymethyl)-benzene

: 303727-85-7
(R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

: 944415-98-9
(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

Guidance literature:: With zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 24h;
DOI:10.1016/j.tet.2007.01.067

Reference yield:

: 934165-89-6
((S)-2-methyl-but-3-ynyloxymethyl)-benzene

: 303727-85-7
(R)-2-[(4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxinan-4-yl]propionaldehyde

: 944415-98-9
(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

: (2S,3R,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

Guidance literature:: With zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 48h; Title compound not separated from byproducts.;
DOI:10.1016/j.tet.2007.01.067

Reference yield:

: 79026-61-2
(R)-3-benzyloxy-2-methylpropanal

: 944415-98-9
(2S,3S,6S)-7-benzyloxy-2-[(2S,4S,5S)-2-(4-methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-6-methyl-hept-4-yn-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium methoxide / tetrahydrofuran; methanol / -78 °C

1.2: 78 percent / tetrahydrofuran; methanol / 0.5 h / -78 °C

2.1: 96 percent / zinc triflate; (-)-(1R,2S)-N-methyl-ephedrine; triethylamine / toluene / 24 h / 20 °C

With sodium methylate; zinc trifluoromethanesulfonate; triethylamine; In tetrahydrofuran; methanol; toluene; 2.1: Carreira asymmetric alkynylation;
DOI:10.1016/j.tet.2007.01.067