(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

Base Information

Chemical Name:(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol
CAS No.:470470-84-9
Molecular Formula:C₃₀H₄₀O₅
Molecular Weight:480.645
Hs Code.:

Synonyms:(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

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Chemical Property of (S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

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Technology Process of (S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

There total 13 articles about (S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-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: 100.0%

: 470470-68-9
(S)-3-Benzyloxy-4-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-2,2-dimethyl-butyraldehyde

: 4301-14-8
acetylenemagnesium bromide

: 470470-84-9
(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

Guidance literature:: In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 470470-84-9
(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / imid.; DMAP; TBAI / 0.5 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

2.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

4.1: 49 percent / LDA / 0.03 h / -78 °C

5.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

6.1: 74 percent / PPTS / 18 h / 20 °C

7.1: 95 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

8.1: 100 percent / (COCl)2; DMSO; Et₃N / -78 °C

9.1: 100 percent / tetrahydrofuran / -78 - 20 °C

With 1H-imidazole; dmap; oxalyl dichloride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7

Reference yield:

: 470470-82-7
((S)-3-benzyloxy-2,2-dimethyl-pent-4-enyloxy)-tert-butyl-dimethyl-silane

: 470470-84-9
(S)-5-Benzyloxy-6-[(4R,6S)-6-(2-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-4,4-dimethyl-hex-1-yn-3-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: BH₃ / tetrahydrofuran / 18 h / -18 - 20 °C

1.2: 67 percent / NaOH; aq. H₂O₂ / 3 h / 50 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.33 h / -78 °C

3.1: 49 percent / LDA / 0.03 h / -78 °C

4.1: 95 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile / 18 h / -20 °C

5.1: 74 percent / PPTS / 18 h / 20 °C

6.1: 95 percent / TBAF / tetrahydrofuran / 18 h / 20 °C

7.1: 100 percent / (COCl)2; DMSO; Et₃N / -78 °C

8.1: 100 percent / tetrahydrofuran / -78 - 20 °C

With oxalyl dichloride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7