Technology Process of (3S,5R,7S,9S,11S,15R)-1,7-dibenzyloxy-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane-3,16-diol
There total 18 articles about (3S,5R,7S,9S,11S,15R)-1,7-dibenzyloxy-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane-3,16-diol 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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470470-73-6
(3S,5R,7S,9S,11S,15R)-1,7-dibenzyloxy-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane-3,16-diol
- Guidance literature:
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(3S,5R,7S,15R,10E)-1,7-dibenzyloxy-15,16-bis-(tert-butyldimethylsilyloxy)-3,5-dihydroxy-8,8-dimethyl-3,5-O-isopropylidene-13-((E)-trimethylsilylmethylidene)hexadec-10-en-9-one;
With
hydrogen fluoride;
In
water; acetonitrile;
at 20 ℃;
for 24h;
trimethyl orthoformate;
With
pyridinium p-toluenesulfonate;
In
methanol;
at 20 ℃;
for 3h;
Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064
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470470-73-6
(3S,5R,7S,9S,11S,15R)-1,7-dibenzyloxy-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane-3,16-diol
- Guidance literature:
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Multi-step reaction with 12 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
10.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C
11.1: 55 percent / ZnI2; 4 Angstroem MS / CH2Cl2 / 18 h / 20 °C / protect from light
12.1: HF / H2O; acetonitrile / 24 h / 20 °C
12.2: 34 percent / PPTS / methanol / 3 h / 20 °C
With
1H-imidazole; dmap; oxalyl dichloride; 4 Angstroem MS; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; zinc(II) iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7
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470470-73-6
(3S,5R,7S,9S,11S,15R)-1,7-dibenzyloxy-5,9-epoxy-11,15-epoxy-13-methylene-9-methoxy-8,8-dimethylhexadecane-3,16-diol
- Guidance literature:
-
Multi-step reaction with 11 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
9.1: 99 percent / Dess-Martin periodinane / CH2Cl2 / 4 h / 20 °C
10.1: 55 percent / ZnI2; 4 Angstroem MS / CH2Cl2 / 18 h / 20 °C / protect from light
11.1: HF / H2O; acetonitrile / 24 h / 20 °C
11.2: 34 percent / PPTS / methanol / 3 h / 20 °C
With
oxalyl dichloride; 4 Angstroem MS; hydrogen fluoride; borane; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; zinc(II) iodide; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide;
In
tetrahydrofuran; dichloromethane; water; acetic acid; acetonitrile;
DOI:10.1016/S0040-4039(02)01054-7
