(R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol

Base Information

• Chemical Name: (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol
• CAS No.: 443912-77-4
• Molecular Formula: C₄₀H₆₈O₈SSi
• Molecular Weight: 737.127
• Mol file: 443912-77-4.mol

Synonyms:(R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol

Chemical Property of (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol

There total 27 articles about (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-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:

tert-Butyl-{(4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy}-dimethyl-silane (443912-60-5) → (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol (443912-77-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

2.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.67 h / -10 °C

3.1: HMPA; n-BuLi / tetrahydrofuran; hexane / -78 - -35 °C

3.2: 18.8 mg / tetrahydrofuran; hexane / 5 h / -35 - 20 °C

4.1: 100 percent / H₂ / Lindlar catalyst / methanol / 6 h / 20 °C

5.1: 96 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) / CH₂Cl₂; 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 20 °C / pH 6

6.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

7.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: 31.0 mg / tetrahydrofuran; hexane / 2 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; hydrogen; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; tert-butyl alcohol; 4.1: Lindlar reduction / 7.2: Julia coupling reaction;

DOI:10.1016/S0040-4020(02)00056-X

Reference yield:

(R)-4-[(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pentan-1-ol (329708-76-1) → (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol (443912-77-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 82 percent / NaH / dimethylformamide / 96 h / -20 °C

2.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

3.1: 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.67 h / -10 °C

4.1: HMPA; n-BuLi / tetrahydrofuran; hexane / -78 - -35 °C

4.2: 18.8 mg / tetrahydrofuran; hexane / 5 h / -35 - 20 °C

5.1: 100 percent / H₂ / Lindlar catalyst / methanol / 6 h / 20 °C

6.1: 96 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) / CH₂Cl₂; 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 20 °C / pH 6

7.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 31.0 mg / tetrahydrofuran; hexane / 2 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 5.1: Lindlar reduction / 8.2: Julia coupling reaction;

DOI:10.1016/S0040-4020(02)00056-X

Reference yield:

Trifluoro-methanesulfonic acid (4R,5R)-5-[(R)-4-(4-methoxy-benzyloxy)-1-methyl-butyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester → (R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-ol (443912-77-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: HMPA; n-BuLi / tetrahydrofuran; hexane / -78 - -35 °C

1.2: 18.8 mg / tetrahydrofuran; hexane / 5 h / -35 - 20 °C

2.1: 100 percent / H₂ / Lindlar catalyst / methanol / 6 h / 20 °C

3.1: 96 percent / 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) / CH₂Cl₂; 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 20 °C / pH 6

4.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

5.2: 31.0 mg / tetrahydrofuran; hexane / 2 h / -78 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; phosphate buffer; hexane; dichloromethane; tert-butyl alcohol; 2.1: Lindlar reduction / 5.2: Julia coupling reaction;

DOI:10.1016/S0040-4020(02)00056-X

upstream raw materials:

(4R,6S)-4-(2-Benzenesulfonyl-ethyl)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxane

(R)-4-{(4R,5R)-5-[(Z)-5-(tert-Butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-pentanal

2-(pent-4-en-1-yl)-1,3-dithiane

bromopentene

Downstream raw materials:

(R)-2-Benzenesulfonyl-6-{(4R,5R)-5-[(Z)-5-(tert-butyl-dimethyl-silanyloxy)-pent-2-enyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-1-((4R,6S)-2,2-dimethyl-6-pent-4-enyl-[1,3]dioxan-4-yl)-heptan-3-one