(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-en-1-ol

Base Information

Chemical Name:(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-en-1-ol
CAS No.:266675-85-8
Molecular Formula:C₂₇H₄₄O₇
Molecular Weight:480.642
Hs Code.:

Synonyms:(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-en-1-ol

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Chemical Property of (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-en-1-ol

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Technology Process of (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-en-1-ol

There total 15 articles about (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-en-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:

Reference yield:

: tert-Butyl-{(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-enyloxy}-diphenyl-silane

: 266675-85-8
(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-en-1-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/ol9904085

Reference yield:

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

: 266675-85-8
(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-en-1-ol

Guidance literature:: Multi-step reaction with 14 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

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; 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;
DOI:10.1021/ol9904085

Reference yield:

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

: 266675-85-8
(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-en-1-ol

Guidance literature:: Multi-step reaction with 13 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

With methanol; dmap; manganese(IV) oxide; osmium(VIII) oxide; lithium aluminium tetrahydride; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; lithium n-butyldiisobutylaluminum hydride; 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;
DOI:10.1021/ol9904085