1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene

Base Information

• Chemical Name: 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene
• CAS No.: 266675-88-1
• Molecular Formula: C₂₄H₃₅NO₆
• Molecular Weight: 433.545

Synonyms:1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene

Chemical Property of 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene

There total 21 articles about 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene 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: 64.0%

(E)-(4S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-6,9-dimethyl-1-nitro-deca-7,9-dien-2-ol (266676-01-1) → 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene (266675-88-1)

Guidance literature:

With copper(l) iodide; dicyclohexyl-carbodiimide; In diethyl ether;

DOI:10.1021/ol9904085

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene (266675-88-1)

Guidance literature:

Multi-step reaction with 20 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

17.1: aq. AcOH

18.1: aq. NaIO₄ / tetrahydrofuran

19.1: KF / propan-2-ol

20.1: 64 percent / DCC; CuI / diethyl ether

With methanol; dmap; manganese(IV) oxide; potassium fluoride; sodium periodate; copper(l) iodide; 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; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; isopropyl alcohol; 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 / 17.1: Hydrolysis / 18.1: oxidative cleavage / 19.1: aldol condensation / 20.1: Dehydration;

DOI:10.1021/ol9904085

Reference yield:

1-but-3-ynyloxymethyl-4-methoxy-benzene (218434-90-3) → 1-Methoxy-4-[(E)-(3R,5R)-5-methoxymethoxy-3-methyl-3-((E)-3-methyl-buta-1,3-dienyl)-8-nitro-oct-7-enyloxymethyl]-benzene (266675-88-1)

Guidance literature:

Multi-step reaction with 19 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

16.1: aq. AcOH

17.1: aq. NaIO₄ / tetrahydrofuran

18.1: KF / propan-2-ol

19.1: 64 percent / DCC; CuI / diethyl ether

With methanol; dmap; manganese(IV) oxide; potassium fluoride; sodium periodate; copper(l) iodide; 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; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; (+)-B-methoxydiisocamphenylborane; In tetrahydrofuran; diethyl ether; dichloromethane; para-xylene; N,N-dimethyl-formamide; isopropyl alcohol; 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 / 16.1: Hydrolysis / 17.1: oxidative cleavage / 18.1: aldol condensation / 19.1: Dehydration;

DOI:10.1021/ol9904085

upstream raw materials:

(E)-(4S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-4-methoxymethoxy-6,9-dimethyl-1-nitro-deca-7,9-dien-2-ol

O-(4-methoxybenzyl)-trichloroacetimidate

1-but-3-ynyloxymethyl-4-methoxy-benzene

(Z)-5-(4-methoxybenzyloxy)-3-methylpent-2-en-1-ol

Downstream raw materials:

(1R,3S,4aS,5S,7Z,8aR)-1-[2-(4-methoxybenzyloxy)-ethyl]-3-methoxymethoxy-1,7-dimethyl-5-nitro-1,2,3,4,4a,5,6,8a-octahydronaphthalene

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