(E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol

Base Information

• Chemical Name: (E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol
• CAS No.: 136262-76-5
• Molecular Formula: C₂₆H₄₂O₅
• Molecular Weight: 434.616

Synonyms:

Chemical Property of (E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol

There total 36 articles about (E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol 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:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal (123444-68-8) → (E)-(1S,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol (136262-76-5)

Guidance literature:

Multi-step reaction with 17 steps

2: DIBAH

3: L-(+)-DIPT, TBHP, TIP / -30 °C

4: Ph₃P, I₂, Im

5: n-BuLi / tetrahydrofuran / -78 deg C to room temp.

7: 1.) O₃, KOH / CH₂Cl₂

8: 78 percent

9: 80 percent / K₂CO₃ / 18-C-6 / toluene

10: Zn(BH₄)2 / diethyl ether / -45 °C

11: tetrahydrofuran / 0 °C

12: 87 percent / HOAc / tetrahydrofuran; H₂O

13: 91 percent / PPTS / acetone

14: 87 percent / NaH / tetrahydrofuran

15: TBAF / tetrahydrofuran

16: Dess-Martin oxidation

17: diethyl ether

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; potassium carbonate; ozone; acetic acid; triphenylphosphine; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; water; acetone; toluene;

DOI:10.1021/jo00019a004

Reference yield:

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal (123444-68-8) → (E)-(1R,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol (136262-76-5)

Guidance literature:

Multi-step reaction with 17 steps

2: DIBAH

3: L-(+)-DIPT, TBHP, TIP / -30 °C

4: Ph₃P, I₂, Im

5: n-BuLi / tetrahydrofuran / -78 deg C to room temp.

7: 1.) O₃, KOH / CH₂Cl₂

8: 78 percent

9: 80 percent / K₂CO₃ / 18-C-6 / toluene

10: Zn(BH₄)2 / diethyl ether / -45 °C

11: tetrahydrofuran / 0 °C

12: 87 percent / HOAc / tetrahydrofuran; H₂O

13: 91 percent / PPTS / acetone

14: 87 percent / NaH / tetrahydrofuran

15: TBAF / tetrahydrofuran

16: Dess-Martin oxidation

17: diethyl ether

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; potassium carbonate; ozone; acetic acid; triphenylphosphine; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; water; acetone; toluene;

DOI:10.1021/jo00019a004

Reference yield:

(3S)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbutanenitrile (136262-53-8) → (E)-(1S,2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-1-phenyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-en-1-ol (136262-76-5)

Guidance literature:

Multi-step reaction with 18 steps

1: DIBAH / diethyl ether

3: DIBAH

4: L-(+)-DIPT, TBHP, TIP / -30 °C

5: Ph₃P, I₂, Im

6: n-BuLi / tetrahydrofuran / -78 deg C to room temp.

8: 1.) O₃, KOH / CH₂Cl₂

9: 78 percent

10: 80 percent / K₂CO₃ / 18-C-6 / toluene

11: Zn(BH₄)2 / diethyl ether / -45 °C

12: tetrahydrofuran / 0 °C

13: 87 percent / HOAc / tetrahydrofuran; H₂O

14: 91 percent / PPTS / acetone

15: 87 percent / NaH / tetrahydrofuran

16: TBAF / tetrahydrofuran

17: Dess-Martin oxidation

18: diethyl ether

With tert.-butylhydroperoxide; potassium hydroxide; n-butyllithium; zinc(II) tetrahydroborate; L-(+)-diisopropyl tartrate; impramine; tetrabutyl ammonium fluoride; iodine; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; isobutyltriphenylphosphonium bromide; potassium carbonate; ozone; acetic acid; triphenylphosphine; 18-crown-6 ether; In tetrahydrofuran; diethyl ether; water; acetone; toluene;

DOI:10.1021/jo00019a004

upstream raw materials:

lithium diphenylcuprate

(E)-(2S,4S,5R,6S)-4,5-Dimethoxy-2,6-dimethyl-8-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-non-7-enal

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

(3S)-4-[(tert-butyldiphenylsilyl)oxy]-3-methylbutanenitrile

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