(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

Base Information

• Chemical Name: (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
• CAS No.: 1335029-16-7
• Molecular Formula: C₂₇H₃₈O₆
• Molecular Weight: 458.595

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 16 articles about (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 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:

C25H42O5Si → (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)

Guidance literature:

Multi-step reaction with 8 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

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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; tert-butyl alcohol;

DOI:10.1002/anie.201101741

Reference yield:

C44H72O8Si2 → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 25 °C

2: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 0.08 h / pH 7 / aq. phosphate buffer; Sonication

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h

With water; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; tert-butyl alcohol;

DOI:10.1002/anie.201101741

Reference yield:

(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 (1335029-15-6) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 0.08 h / pH 7 / aq. phosphate buffer; Sonication

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h

With water; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; tert-butyl alcohol;

DOI:10.1002/anie.201101741

upstream raw materials:

(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

(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol

(3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-one

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

(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

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