(2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

Base Information

• Chemical Name: (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one
• CAS No.: 161466-52-0
• Molecular Formula: C₃₈H₅₂O₅Si
• Molecular Weight: 616.913
• Mol file: 161466-52-0.mol

Synonyms:(2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

Chemical Property of (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

There total 6 articles about (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-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: 70.0%

(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-[2-((1S,2S,6S,8aR)-2,6-dimethyl-8-triethylsilanyloxy-1,2,6,8a-tetrahydro-naphthalen-1-yl)-ethyl]-2,2-dimethyl-[1,3]dioxane (161466-50-8) → (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (161466-52-0)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate;

DOI:10.1021/jo00110a051

Reference yield:

<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol (116996-45-3) → (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (161466-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / Swern oxidation

2: 99 percent / LDA, BuLi / tetrahydrofuran

3: 70 percent / m-CPBA, NaHCO₃ / ethyl acetate

With n-butyllithium; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate;

DOI:10.1021/jo00110a051

Reference yield:

lovastatin (75330-75-5,79952-44-6) → (2S,3S,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-2-hydroxy-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (161466-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / LiAlH₄ / tetrahydrofuran / 5 h

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

3: 82 percent / p-TsOH*H₂O

4: 87 percent / Swern oxidation

5: 99 percent / LDA, BuLi / tetrahydrofuran

6: 70 percent / m-CPBA, NaHCO₃ / ethyl acetate

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00110a051

upstream raw materials:

(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-[2-((1S,2S,6S,8aR)-2,6-dimethyl-8-triethylsilanyloxy-1,2,6,8a-tetrahydro-naphthalen-1-yl)-ethyl]-2,2-dimethyl-[1,3]dioxane

<1S-<1α,3α,7β,8β(4S^*,6R^*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol

lovastatin

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-7-(1,2,6,7,8,8a-Hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-1,3,5-heptanetriol

Downstream raw materials:

(1R,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-[(S)-2-methyl-3-oxo-prop-(Z)-ylidene]-cyclohex-3-enecarboxylic acid methyl ester