4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

Base Information

Chemical Name:4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane
CAS No.:266675-86-9
Molecular Formula:C₂₇H₄₂O₆
Molecular Weight:462.627
Hs Code.:

Synonyms:4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of 4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

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Technology Process of 4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

There total 17 articles about 4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane 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:

: Methanesulfonic acid (E)-(2S,5R,7S)-8-(2,2-dimethyl-[1,3]dioxolan-4-yl)-5-[2-(4-methoxy-benzyloxy)-ethyl]-7-methoxymethoxy-2,5-dimethyl-oct-3-enyl ester

: 266675-86-9
4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1021/ol9904085

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 266675-86-9
4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 16 steps

1.1: TfOH / diethyl ether / 20 °C

2.1: nBuLi / tetrahydrofuran / -78 - 20 °C

3.1: tetrahydrofuran / -45 °C

4.1: LiAlH₄ / diethyl ether / 0 °C

5.1: MnO₂ / CH₂Cl₂

5.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

6.1: 86 percent / LiBH₄; MeOH / diethyl ether

7.1: 84 percent / Et₃N; DMAP / CH₂Cl₂

8.1: 89 percent / p-xylene / 100 °C

9.1: LiAl(nBu)iBu₂H / tetrahydrofuran / 20 °C

10.1: (+)-(lpc)2BOCH₃ / diethyl ether / -78 °C

11.1: 86 percent / iPr₂NEt / CH₂Cl₂

12.1: 79 percent / OsO₄; NMO; H₂O / acetone; 2-methyl-propan-2-ol

13.1: TsOH / dimethylformamide / 20 °C

14.1: TBAF / tetrahydrofuran / 20 °C

15.1: Et₃N; DMAP / CH₂Cl₂

16.1: KOtBu / tetrahydrofuran / 0 - 20 °C

With methanol; dmap; manganese(IV) oxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; lithium n-butyldiisobutylaluminum hydride; trifluorormethanesulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 4.1: Reduction / 5.1: Oxidation / 5.2: Evans aldolization / 6.1: cleavage / 7.1: silylation / 8.1: Eschenmoser-Claisen rearrangement / 9.1: Reduction / 10.1: Grignard reaction / 11.1: Etherification / 12.1: Oxidation / 13.1: Etherification / 14.1: desilylation / 15.1: Substitution / 16.1: Elimination;
DOI:10.1021/ol9904085

Reference yield:

: 218434-90-3
1-but-3-ynyloxymethyl-4-methoxy-benzene

: 266675-86-9
4-{(E)-(2S,4R)-4-[2-(4-Methoxy-benzyloxy)-ethyl]-2-methoxymethoxy-4,7-dimethyl-octa-5,7-dienyl}-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 15 steps

1.1: nBuLi / tetrahydrofuran / -78 - 20 °C

2.1: tetrahydrofuran / -45 °C

3.1: LiAlH₄ / diethyl ether / 0 °C

4.1: MnO₂ / CH₂Cl₂

4.2: 74 percent / Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

5.1: 86 percent / LiBH₄; MeOH / diethyl ether

6.1: 84 percent / Et₃N; DMAP / CH₂Cl₂

7.1: 89 percent / p-xylene / 100 °C

8.1: LiAl(nBu)iBu₂H / tetrahydrofuran / 20 °C

9.1: (+)-(lpc)2BOCH₃ / diethyl ether / -78 °C

10.1: 86 percent / iPr₂NEt / CH₂Cl₂

11.1: 79 percent / OsO₄; NMO; H₂O / acetone; 2-methyl-propan-2-ol

12.1: TsOH / dimethylformamide / 20 °C

13.1: TBAF / tetrahydrofuran / 20 °C

14.1: Et₃N; DMAP / CH₂Cl₂

15.1: KOtBu / tetrahydrofuran / 0 - 20 °C

With methanol; dmap; manganese(IV) oxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; lithium n-butyldiisobutylaluminum hydride; potassium tert-butylate; tetrabutyl ammonium fluoride; water; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Substitution / 2.1: Addition / 3.1: Reduction / 4.1: Oxidation / 4.2: Evans aldolization / 5.1: cleavage / 6.1: silylation / 7.1: Eschenmoser-Claisen rearrangement / 8.1: Reduction / 9.1: Grignard reaction / 10.1: Etherification / 11.1: Oxidation / 12.1: Etherification / 13.1: desilylation / 14.1: Substitution / 15.1: Elimination;
DOI:10.1021/ol9904085