Technology Process of (2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol
There total 38 articles about (2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol 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:
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![(2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol](/Databaselist/images/loading.webp)
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1335029-18-9
(2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol
- Guidance literature:
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With
water; acetic acid;
In
tetrahydrofuran;
at 55 ℃;
for 40h;
DOI:10.1002/anie.201101741
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1335029-18-9
(2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol
- Guidance literature:
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Multi-step reaction with 9 steps
1.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 16 h
2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 - 25 °C
2.2: 0.5 h / -78 °C
2.3: -78 - 25 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C
3.2: 16 h / 0 - 20 °C
4.1: pyridine; sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 2 h
5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere
5.2: 0.75 h / -78 °C / Inert atmosphere
5.3: -78 - 20 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.17 h
7.2: 20.17 h
8.1: borane-THF; ethane / tetrahydrofuran; toluene / 0.12 h / 0 °C / Inert atmosphere
8.2: 0 - 20 °C / Inert atmosphere
9.1: water; acetic acid / tetrahydrofuran / 40 h / 55 °C
With
pyridine; sodium periodate; osmium(VIII) oxide; borane-THF; ethane; carbon tetrabromide; water; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile; mineral oil; pentane;
7.1: Horner-Wadsworth-Emmons olefination / 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201101741
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1335029-18-9
(2S)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropane-1,2-diol
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h
2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / dichloromethane / 12 h
3.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C
3.2: 1 h / -78 °C
3.3: -78 - 20 °C
4.1: dmap; triethylamine / dichloromethane / 0.83 h / 0 °C
5.1: copper(l) iodide / diethyl ether / -78 - -30 °C / Inert atmosphere
5.2: 1 h / -78 °C / Inert atmosphere
5.3: -78 - 20 °C
6.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 25 °C
7.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 0.08 h / pH 7 / aq. phosphate buffer; Sonication
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h
9.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.17 h
9.2: 20.17 h
10.1: borane-THF; ethane / tetrahydrofuran; toluene / 0.12 h / 0 °C / Inert atmosphere
10.2: 0 - 20 °C / Inert atmosphere
11.1: water; acetic acid / tetrahydrofuran / 40 h / 55 °C
With
dmap; copper(l) iodide; n-butyllithium; borane-THF; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ethane; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride;
In
tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; tert-butyl alcohol;
9.1: Horner-Wadsworth-Emmons olefination / 9.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201101741
