(6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one

Base Information

• Chemical Name: (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one
• CAS No.: 1335029-17-8
• Molecular Formula: C₆₉H₉₄O₁₃
• Molecular Weight: 1131.5
• Mol file: 1335029-17-8.mol

Synonyms:

Chemical Property of (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one

There total 34 articles about (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one 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: 89.0%

(S)-2-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)propanal (1335029-16-7) + dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate (1335028-86-8) → (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one (1335029-17-8)

Guidance literature:

dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; for 0.166667h;

(S)-2-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)propanal; In acetonitrile; for 20.1667h;

DOI:10.1002/anie.201101741

Reference yield:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (1039455-95-2) → (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one (1335029-17-8)

Guidance literature:

Multi-step reaction with 7 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

With pyridine; sodium periodate; osmium(VIII) oxide; carbon tetrabromide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetonitrile; mineral oil; pentane; 7.1: Horner-Wadsworth-Emmons olefination / 7.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1002/anie.201101741

Reference yield:

C25H42O5Si → (6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one (1335029-17-8)

Guidance literature:

Multi-step reaction with 9 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

With dmap; copper(l) iodide; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; acetonitrile; tert-butyl alcohol; 9.1: Horner-Wadsworth-Emmons olefination / 9.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1002/anie.201101741

upstream raw materials:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

(2S,6R,8S,11R)-11-(benzyloxy)-2-((R)-1-((4-methoxybenzyl)oxy)propan-2-yl)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-ene

(2S,5R,10S,11R)-5-(benzyloxy)-2-hydroxy-12-((4-methoxybenzyl)oxy)-11-methyl-10-((triethylsilyl)oxy)-1-((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)dodec-7-yn-6-one

(S)-2-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((S)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)propanal

Downstream raw materials:

(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

(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-hydroxy-2-methylpropanoic acid