(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

Base Information

Chemical Name:(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol
CAS No.:1354396-54-5
Molecular Formula:C₂₁H₃₀O₅
Molecular Weight:362.466
Hs Code.:

Synonyms:(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

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Chemical Property of (S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

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Technology Process of (S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

There total 14 articles about (S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-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: 84.0%

: 1354396-53-4
1-{(4S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-one

: 1354396-54-5
(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

Guidance literature:: With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -30 ℃; for 2.75h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol203114a

Reference yield:

: 1354396-53-4
1-{(4S,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-one

: 1354396-55-6
(R)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

: 1354396-54-5
(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

Guidance literature:: With dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; at -30 ℃; for 2.5h; optical yield given as %de; diastereoselective reaction;
DOI:10.1021/ol203114a

Reference yield:

: 1354396-51-2
(E)-1-(4-methoxybenzyloxy)dec-3-en-6-yn-5-one

: 1354396-54-5
(S)-1-{(4R,5R)-5-[2-(4-methoxybenzyloxy)ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}hex-2-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: AD-mix-β; methanesulfonamide; water / tert-butyl alcohol / 18 h / 0 °C

2: toluene-4-sulfonic acid / 12 h / 20 °C

3: dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 2.75 h / -30 °C

With methanesulfonamide; dimethylsulfide borane complex; AD-mix-β; water; toluene-4-sulfonic acid; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; tert-butyl alcohol;
DOI:10.1021/ol203114a