methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate

Base Information

• Chemical Name: methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate
• CAS No.: 290813-02-4
• Molecular Formula: C₄₁H₅₈O₁₀
• Molecular Weight: 710.906

Synonyms:methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate

Chemical Property of methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate

There total 13 articles about methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1⁽⁹⁾-en-4-carboxylate 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: 51.0%

methyl cyanoformate (17640-15-2) + (-)-(1S,5R,8R,9S)-5-(4-methoxy-benzyloxymethyl)-9-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-(E)-oct-6-enyl-bicyclo[4.3.1]dec-6-ene-2,10-dione (290813-01-3) → methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1(9)-en-4-carboxylate (290813-02-4)

Guidance literature:

(-)-(1S,5R,8R,9S)-5-(4-methoxy-benzyloxymethyl)-9-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-(E)-oct-6-enyl-bicyclo[4.3.1]dec-6-ene-2,10-dione; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.666667h;

With magnesium bromide; In various solvents; at -78 ℃; for 0.5h;

methyl cyanoformate; In various solvents; at -78 - 0 ℃; for 1.25h; Further stages.;

DOI:10.1021/ja001958x

Reference yield:

2-(R)-oxiranyl-2-((E)-pent-3-enyl)-[1,3]dioxolane (290813-16-0) → methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1(9)-en-4-carboxylate (290813-02-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - 0 °C

1.2: boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 0.75 h / -78 °C

1.3: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 20 °C

3.1: 88 percent / potassium carbonate / methanol / 12 h / 20 °C

4.1: bis(cyclopentadienyl) zirconium chloride hydride / CH₂Cl₂ / 0.67 h / 20 °C

4.2: 81 percent / N-bromosuccinimide / CH₂Cl₂ / 2 h / 0 °C

5.1: t-BuLi / diethyl ether; pentane / 0.67 h / -78 °C

5.2: MgBr₂ / diethyl ether; tetrahydrofuran / 0.75 h / -78 - 23 °C

5.3: 53 percent / diethyl ether; tetrahydrofuran; toluene / -78 - 23 °C

6.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

6.2: magnesium bromide / various solvents / 0.5 h / -78 °C

6.3: 51 percent / various solvents / 1.25 h / -78 - 0 °C

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; tert.-butyl lithium; potassium hexamethylsilazane; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; pentane; 5.2: Grignard reaction / 5.3: Dieckmann-like cyclization;

DOI:10.1021/ja001958x

Reference yield:

(R)-1-((E)-2-(pent-3-enyl)-[1,3]dioxolan-2-yl)-ethane-1,2-diol (290813-15-9) → methyl (2R,6S,7S,8S)-2-(4-methoxy-benzyloxymethyl)-7-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-[(E)-oct-6-enyl]-5,10-dioxo-bicyclo[4.3.1]dec-1(9)-en-4-carboxylate (290813-02-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH / tetrahydrofuran / 0.33 h / 0 °C

1.2: 92 percent / tosyl imidazole / tetrahydrofuran / 4 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 - 0 °C

2.2: boron trifluoride diethyl etherate / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.3: 85 percent / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 72 h / 20 °C

4.1: 88 percent / potassium carbonate / methanol / 12 h / 20 °C

5.1: bis(cyclopentadienyl) zirconium chloride hydride / CH₂Cl₂ / 0.67 h / 20 °C

5.2: 81 percent / N-bromosuccinimide / CH₂Cl₂ / 2 h / 0 °C

6.1: t-BuLi / diethyl ether; pentane / 0.67 h / -78 °C

6.2: MgBr₂ / diethyl ether; tetrahydrofuran / 0.75 h / -78 - 23 °C

6.3: 53 percent / diethyl ether; tetrahydrofuran; toluene / -78 - 23 °C

7.1: KHMDS / tetrahydrofuran; toluene / 0.67 h / -78 °C

7.2: magnesium bromide / various solvents / 0.5 h / -78 °C

7.3: 51 percent / various solvents / 1.25 h / -78 - 0 °C

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; tert.-butyl lithium; potassium hexamethylsilazane; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; pentane; 6.2: Grignard reaction / 6.3: Dieckmann-like cyclization;

DOI:10.1021/ja001958x

upstream raw materials:

methyl cyanoformate

(-)-(1S,5R,8R,9S)-5-(4-methoxy-benzyloxymethyl)-9-[(R)-2-methoxymethoxy-2-((E)-2-pent-3-enyl-[1,3]dioxolan-2-yl)-ethyl]-8-(E)-oct-6-enyl-bicyclo[4.3.1]dec-6-ene-2,10-dione

2-(R)-oxiranyl-2-((E)-pent-3-enyl)-[1,3]dioxolane

(R)-1-((E)-2-(pent-3-enyl)-[1,3]dioxolan-2-yl)-ethane-1,2-diol

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