Technology Process of 1-{2,2-dimethyl-6-[2,2,5-trimethyl-6-(2-triisopropylsilanyloxy-ethyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dioxan-4-yl}-5-{6-[4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol
There total 11 articles about 1-{2,2-dimethyl-6-[2,2,5-trimethyl-6-(2-triisopropylsilanyloxy-ethyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dioxan-4-yl}-5-{6-[4-(4-methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-pentane-2,4-diol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one;
With
trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine;
In
dichloromethane;
at 0 ℃;
for 1h;
{(4S,6R)-2,2-Dimethyl-6-[(4R,5S,6S)-2,2,5-trimethyl-6-(2-triisopropylsilanyloxy-ethyl)-[1,3]dioxan-4-ylmethyl]-[1,3]dioxan-4-yl}-acetaldehyde;
With
boron trifluoride diethyl etherate;
In
dichloromethane;
at -78 ℃;
for 1.25h;
With
acetic acid; tetramethylammonium triacetoxyborohydride;
In
tetrahydrofuran; acetonitrile;
at -20 ℃;
for 10h;
Further stages. Title compound not separated from byproducts.;
DOI:10.1021/ja0035102
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: KO-t-Bu; n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 - -45 °C
1.2: (+)-B-methoxydiisopinocampheylborane; BF3*OEt2 / tetrahydrofuran; hexane; diethyl ether / -78 - -30 °C
1.3: NaOH; H2O2 / various solvents / -30 - -20 °C
2.1: n-BuLi; SiHCl3 / tetrahydrofuran; hexane / 0.75 h / -78 °C
2.2: tetrahydrofuran; diethyl ether; hexane / -78 - 0 °C
3.1: Rh(acac)(CO)2 / benzene / 28 h / 60 °C / 51716.2 Torr
3.2: NaHCO3; H2O2 / H2O; tetrahydrofuran; methanol / 1.5 h / Heating
4.1: 75 percent / camphorsulfonic acid / 16 h
5.1: HgClOAc; Yb(OTf)3 / 0.67 h / 0 °C
5.2: 0.26 g / DABCO; tris(2,4-di-tert-butylphenyl)phosphite; H2 / Rh(acac)(CO)2 / ethyl acetate / 48 h / 60 °C / 51716.2 Torr
6.1: N,N-diisopropylethylamine; TMSOTf / CH2Cl2 / 1 h / 0 °C
6.2: BF3*OEt2 / CH2Cl2 / 1.25 h / -78 °C
6.3: Me4NBH(OAc)3; AcOH / tetrahydrofuran; acetonitrile / 10 h / -20 °C
With
acetylacetonatodicarbonylrhodium(l); n-butyllithium; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; trichlorosilane; potassium tert-butylate; chloro(acetato)mercury(II); N-ethyl-N,N-diisopropylamine; ytterbium(III) triflate;
In
tetrahydrofuran; hexane; dichloromethane; benzene;
1.1: Brown's asymmetric crotylation;
DOI:10.1021/ja0035102
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: KH / tetrahydrofuran / 16 h
1.2: pyridinium p-toluenesulfonic acid / acetone; H2O / 1 h / Heating
2.1: (+)-B-methoxydiisopinocampheylborane / diethyl ether / -78 - 20 °C
2.2: diethyl ether / 3 h / -90 - 20 °C
2.3: 71 percent / NaOH; H2O2 / diethyl ether; H2O / 1 h / Heating
3.1: HgClOAc; Yb(OTf)3 / -78 - 0 °C
3.2: DABCO; tris(2,4-di-tert-butylphenyl)phosphite; H2 / Rh(acac)(CO)2 / ethyl acetate / 24 h / 50 °C / 41372.9 Torr
4.1: diethyl ether / 0.5 h / 0 °C
5.1: 0.35 g / Dess-Martin periodinane / CH2Cl2 / 1 h
6.1: N,N-diisopropylethylamine; TMSOTf / CH2Cl2 / 1 h / 0 °C
6.2: BF3*OEt2 / CH2Cl2 / 1.25 h / -78 °C
6.3: Me4NBH(OAc)3; AcOH / tetrahydrofuran; acetonitrile / 10 h / -20 °C
With
(+)-Ipc2BOMe; trimethylsilyl trifluoromethanesulfonate; potassium hydride; chloro(acetato)mercury(II); Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; ytterbium(III) triflate;
In
tetrahydrofuran; diethyl ether; dichloromethane;
2.1: Brown's asymmetric allylation;
DOI:10.1021/ja0035102
![1-{(4S,6R)-6-[(E)-(3S,4S)-4-(4-Methoxy-benzyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-propan-2-one](/Databaselist/images/loading.webp)
