(1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol

Base Information

• Chemical Name: (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol
• CAS No.: 1333237-62-9
• Molecular Formula: C₃₈H₅₂Cl₈O₆Si
• Molecular Weight: 916.537

Synonyms:(1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol

Chemical Property of (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol

There total 26 articles about (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-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: 50.0%

(3R,4S,5R,6S,Z)-1-((4S,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-di-methyl-1,3-dioxan-4-yl)-3,5,6-trichloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)hept-1-en-4-ol (1333237-61-8) → (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol (1333237-62-9)

Guidance literature:

With tetraethylammonium trichloride; In dichloromethane; at 0 - 20 ℃; for 73h; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

C25H37NOSi → (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol (1333237-62-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: N-chloro-succinimide / tetrachloromethane; dichloromethane / 24.17 h / 0 - 20 °C / Darkness; Inert atmosphere

2.1: hydrogenchloride; water / 3 h / 20 °C / Inert atmosphere

3.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 20 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

3.3: 0.5 h / 20 °C / Inert atmosphere

4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C / Inert atmosphere

4.2: -78 °C / Inert atmosphere

5.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / nonane; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

7.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.2: 0.08 h / 0 - 20 °C / Inert atmosphere

8.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

8.2: 0.17 h / -78 - 20 °C / Inert atmosphere

9.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

10.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C

11.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.75 h / 0 - 20 °C / Inert atmosphere

12.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15.5 h / 20 °C / Inert atmosphere

13.1: sodium hexamethyldisilazane / toluene / 17.5 h / -78 - 20 °C / Inert atmosphere

14.1: dichlorotriphenylphosphorane / dichloromethane / 5.25 h / 0 - 20 °C / Inert atmosphere

15.1: tetraethylammonium trichloride / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; N-chloro-succinimide; bis(acetylacetonate)oxovanadium; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; (-)-N-methylephedrine; water; hydrogen; sodium hexamethyldisilazane; tetraethylammonium trichloride; pyridinium p-toluenesulfonate; zirconium(IV) chloride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; dichlorotriphenylphosphorane; In tetrahydrofuran; methanol; tetrachloromethane; nonane; dichloromethane; ethyl acetate; toluene; 6.1: Dess-Martin oxidation / 11.1: Mitsunobu reaction / 13.1: Julia-Kocienski olefination;

DOI:10.1002/anie.201102521

Reference yield:

C25H35Cl2NOSi → (1R,2R,3S,4R,5R,6S)-1-((4R,5S,6R)-6-(4-(tert-butyldiphenylsilyloxy)-1,1-dichlorobutyl)-5-chloro-2,2-dimethyl-1,3-dioxan-4-yl)-1,2,3,5,6-pentachloro-7-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)heptan-4-ol (1333237-62-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: hydrogenchloride; water / 3 h / 20 °C / Inert atmosphere

2.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 0.25 h / 20 °C / Inert atmosphere

2.2: 18 h / 20 °C / Inert atmosphere

2.3: 0.5 h / 20 °C / Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / -78 - 20 °C / Inert atmosphere

3.2: -78 °C / Inert atmosphere

4.1: tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium / nonane; dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: zirconium(IV) chloride / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

6.2: 0.08 h / 0 - 20 °C / Inert atmosphere

7.1: sodium tetrahydroborate / methanol / 1.33 h / -78 °C / Inert atmosphere

7.2: 0.17 h / -78 - 20 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / dichloromethane / 24.67 h / 0 - 20 °C / Inert atmosphere

9.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 16 h / 20 °C

10.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 1.75 h / 0 - 20 °C / Inert atmosphere

11.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 15.5 h / 20 °C / Inert atmosphere

12.1: sodium hexamethyldisilazane / toluene / 17.5 h / -78 - 20 °C / Inert atmosphere

13.1: dichlorotriphenylphosphorane / dichloromethane / 5.25 h / 0 - 20 °C / Inert atmosphere

14.1: tetraethylammonium trichloride / dichloromethane / 73 h / 0 - 20 °C / Inert atmosphere

With hydrogenchloride; tert.-butylhydroperoxide; sodium tetrahydroborate; bis(acetylacetonate)oxovanadium; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; (-)-N-methylephedrine; water; hydrogen; sodium hexamethyldisilazane; tetraethylammonium trichloride; pyridinium p-toluenesulfonate; zirconium(IV) chloride; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; dichlorotriphenylphosphorane; In tetrahydrofuran; methanol; nonane; dichloromethane; ethyl acetate; toluene; 5.1: Dess-Martin oxidation / 10.1: Mitsunobu reaction / 12.1: Julia-Kocienski olefination;

DOI:10.1002/anie.201102521

upstream raw materials:

(R)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-5,5-dichlorooct-2-yn-4-ol

(R,e)-1-(benzyloxy)-8-(tert-butyldiphenylsilyloxy)-5,5-dichlorooct-2-en-4-ol

(R)-1-((2S,3S)-3-(benzyloxymethyl)oxiran-2-yl)-5-(tert-butyldiphenylsilyloxy)-2,2-dichloropentan-1-ol

1-((2R,3S)-3-((benzyloxy)methyl)oxiran-2-yl)-5-((tert-butyldiphenylsilyl)oxy)-2,2-dichloropentan-1-one

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