(2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one

Base Information

• Chemical Name: (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one
• CAS No.: 845780-33-8
• Molecular Formula: C₃₈H₆₈O₆Si₂
• Molecular Weight: 677.125
• Mol file: 845780-33-8.mol

Synonyms:(2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one

Chemical Property of (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one

There total 10 articles about (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-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:

(2R,4R)-4-[(2S,4R,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-2-methyl-pentanal + (3R,4S,5S)-[4,6-bis(tert-butyldimethylsilanyloxy)-3,5-dimethyl-2-oxohexyl]phosphonic acid dimethyl ester (845780-32-7) → (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one (845780-33-8)

Guidance literature:

With barium dihydroxide; In tetrahydrofuran; water; at 20 ℃; for 6h;

DOI:10.1021/ol0478279

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one (845780-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

2: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

With barium dihydroxide; In tetrahydrofuran; hexane; n-heptane; water; 2: Horner-Wadsworth-Emmons coupling;

DOI:10.1021/ol0478279

Reference yield:

(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one (444105-66-2) → (2S,3S,4R,8R,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundec-6-en-5-one (845780-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: LDA / tetrahydrofuran; hexane; heptane / 0.5 h / -78 °C

2.1: 818 mg / tetrahydrofuran; hexane; heptane / -78 - 20 °C

3.1: 83 mg / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 6 h / 20 °C

With barium dihydroxide; n-butyllithium; In tetrahydrofuran; hexane; n-heptane; water; 3.1: Horner-Wadsworth-Emmons coupling;

DOI:10.1021/ol0478279

upstream raw materials:

(3R,4S,5S)-[4,6-bis(tert-butyldimethylsilanyloxy)-3,5-dimethyl-2-oxohexyl]phosphonic acid dimethyl ester

tert-butyldimethylsilyl chloride

(3R,4S,5S)-4-[(tert-butyldimethylsilanyl)oxy]-3,5-dimethyltetrahydropyran-2-one

(S)-2-[(2S,4S,5S)-2-(4-Methoxy-phenyl)-5-methyl-[1,3]dioxan-4-yl]-propionaldehyde

Downstream raw materials:

(2S,3S,4R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-one

(2S,3S,4S,5R,8S,10R)-1,3-bis(tert-butyldimethylsilanyloxy)-10-[(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]-2,4,8-trimethylundecan-5-ol

(2S,4R,5S)-2-(4-methoxyphenyl)-5-methyl-4-[(1R,3S,6R,7S,8S,9S)-6,8,10-tris(tert-butyldimethylsilanyloxy)-1,3,7,9-tetramethyldecyl]-[1,3]dioxane

1-methoxy-4-{(1R,2S)-2-methyl-1-[(1R,3S,6R,7S,8S,9S)-6,8,10-tris(tert-butyldimethylsilanyloxy)-1,3,7,9-tetramethyldecyl]but-3-enyloxymethyl}benzene