(-)-(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

Base Information

Chemical Name:(-)-(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
CAS No.:290813-01-3
Molecular Formula:C₃₉H₅₆O₈
Molecular Weight:652.869
Hs Code.:

(-)-(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

Synonyms:(-)-(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

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Chemical Property of (-)-(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

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Technology Process of (-)-(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

There total 11 articles about (-)-(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 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: 53.0%

: 1-((1E,8E)-deca-1,8-dienyl)-2-(4-methoxy-benzyloxymethyl)-5-oxocyclopentanecarboxylic acid methyl ester

: 290812-99-6
2-((R)-(E)-4-bromo-1-methoxymethoxy-but-3-enyl)-2-((E)-pent-3-enyl)-[1,3]dioxolane

: (-)-(1R,5S,8S,9R)-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
(-)-(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

Guidance literature:: 2-((R)-(E)-4-bromo-1-methoxymethoxy-but-3-enyl)-2-((E)-pent-3-enyl)-[1,3]dioxolane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 0.666667h;

With magnesium bromide; In tetrahydrofuran; diethyl ether; at -78 - 23 ℃; for 0.75h;

1-((1E,8E)-deca-1,8-dienyl)-2-(4-methoxy-benzyloxymethyl)-5-oxocyclopentanecarboxylic acid methyl ester; In tetrahydrofuran; diethyl ether; toluene; at -78 - 23 ℃; Further stages.;
DOI:10.1021/ja001958x

Reference yield:

: 290813-16-0
2-(R)-oxiranyl-2-((E)-pent-3-enyl)-[1,3]dioxolane

: 290813-01-3
(-)-(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

Guidance literature:: Multi-step reaction with 5 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

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; tert.-butyl lithium; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 5.2: Grignard reaction / 5.3: Dieckmann-like cyclization;
DOI:10.1021/ja001958x

Reference yield:

: 290813-15-9
(R)-1-((E)-2-(pent-3-enyl)-[1,3]dioxolan-2-yl)-ethane-1,2-diol

: 290813-01-3
(-)-(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

Guidance literature:: Multi-step reaction with 6 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

With 2,6-dimethylpyridine; Schwartz's reagent; n-butyllithium; tert.-butyl lithium; sodium hydride; potassium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 6.2: Grignard reaction / 6.3: Dieckmann-like cyclization;
DOI:10.1021/ja001958x