Technology Process of (S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pentyl]-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propan-1-ol
There total 34 articles about (S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pentyl]-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propan-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:
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565226-33-7
(S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pentyl]-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propan-1-ol
- Guidance literature:
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With
tetrabutyl ammonium fluoride;
In
tetrahydrofuran;
at 20 ℃;
for 3h;
DOI:10.1016/S0040-4039(03)00955-9
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565226-33-7
(S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pentyl]-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propan-1-ol
- Guidance literature:
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Multi-step reaction with 19 steps
1.1: 73 percent / KH; 18-crown-6 / 3 h / 25 °C
2.1: OsO4; NMO / acetone; H2O / 20 h / 25 °C
3.1: NaIO4 / acetone; H2O / 20 h / 25 °C
4.1: BF3*OEt2 / CH2Cl2 / 6 h / -90 - -30 °C
5.1: TsOH / benzene / 14 h / 25 °C
6.1: OsO4; NMO / acetone; H2O / 20 h / 25 °C
7.1: NaIO4 / acetone; H2O / 1 h / 20 °C
8.1: LiAlH4 / diethyl ether / 0.25 h / 0 °C
9.1: imidazole / CH2Cl2 / 1 h / 25 °C
10.1: H2 / Raney Ni (W-2) / ethanol / 120 h / 25 °C
11.1: pyridine; DMAP / CH2Cl2 / 20 h / 20 °C
12.1: NaI; NaHCO3 / butan-2-one / 20 h / 60 °C
13.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C
13.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C
14.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
15.1: t-BuOK / toluene / 1.5 h / 95 °C
16.1: TBAF / tetrahydrofuran / 10 h / 20 °C
17.1: imidazole / CH2Cl2 / 0.25 h / 20 °C
18.1: CSA / CH2Cl2 / 1 h / 15 °C
19.1: TBAF / tetrahydrofuran / 3 h / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 18-crown-6 ether; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; sodium iodide;
Raney Ni (W-2);
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; butanone; pentane; benzene;
15.1: Wittig reaction;
DOI:10.1016/S0040-4039(03)00955-9
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565226-33-7
(S)-2-((4R,5R,6S)-6-{(S)-3-[(2S,4R,5R,6S)-6-[(1S,2R,3S,4S)-4-Benzyloxy-2-(4-methoxy-benzyloxy)-1,3-dimethyl-pentyl]-5-methyl-2-(2,4,6-trimethyl-phenyl)-[1,3]dioxan-4-yl]-1-methyl-but-3-enyl}-2,2,5-trimethyl-[1,3]dioxan-4-yl)-propan-1-ol
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: imidazole / CH2Cl2 / 1 h / 25 °C
2.1: H2 / Raney Ni (W-2) / ethanol / 120 h / 25 °C
3.1: pyridine; DMAP / CH2Cl2 / 20 h / 20 °C
4.1: NaI; NaHCO3 / butan-2-one / 20 h / 60 °C
5.1: t-BuLi / pentane; diethyl ether / 1 h / -78 - 20 °C
5.2: 78 percent / pentane; diethyl ether / 1.5 h / -78 °C
6.1: Dess-Martin periodinane / CH2Cl2 / 2 h / 20 °C
7.1: t-BuOK / toluene / 1.5 h / 95 °C
8.1: TBAF / tetrahydrofuran / 10 h / 20 °C
9.1: imidazole / CH2Cl2 / 0.25 h / 20 °C
10.1: CSA / CH2Cl2 / 1 h / 15 °C
11.1: TBAF / tetrahydrofuran / 3 h / 20 °C
With
pyridine; 1H-imidazole; dmap; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; sodium iodide;
Raney Ni (W-2);
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; butanone; pentane;
7.1: Wittig reaction;
DOI:10.1016/S0040-4039(03)00955-9