((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

Base Information

Chemical Name:((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate
CAS No.:1333237-05-0
Molecular Formula:C₃₅H₆₀Cl₄O₆Si₂
Molecular Weight:774.841
Hs Code.:

((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

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Chemical Property of ((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

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Technology Process of ((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

There total 21 articles about ((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate 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: 12.0%

: 1333237-02-7
((2S,3S)-3-((1R,2S,4S,9R,10S,z)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2-dichloroundec-5-enyl)oxiran-2-yl)methyl acetate

: C₂₈H₅₃Cl₃O₆Si₂

: ((2S,3S)-3-((1R,2S,4S,5S,6S,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

: 1333237-05-0
((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

Guidance literature:: With tetraethylammonium trichloride; In dichloromethane; at -78 ℃; for 1h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/anie.201102521

Reference yield:

: 1333236-45-5
(4R,5S,E)-4,5-dichloro-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)hex-2-en-1-ol

: C₂₈H₅₃Cl₃O₆Si₂

: ((2S,3S)-3-((1R,2S,4S,5S,6S,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

: 1333237-05-0
((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

Guidance literature:: Multi-step reaction with 9 steps

1.1: dmap; triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.1: AD-mix-β; methanesulfonamide; water / tert-butyl alcohol / 46 h / 0 - 4 °C / Inert atmosphere

3.1: 1,4-diaza-bicyclo[2.2.2]octane; trifluoromethylsulfonic anhydride / dichloromethane / 19 h / -78 - 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / methanol / 2 h / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -15 °C / Inert atmosphere

6.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 15 h / 0 - 4 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

8.1: potassium hexamethylsilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

8.2: 1 h / -78 - 0 °C / Inert atmosphere

9.1: tetraethylammonium trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; methanesulfonamide; pyridine hydrofluoride; trifluoromethylsulfonic anhydride; AD-mix-β; camphor-10-sulfonic acid; water; tetraethylammonium trichloride; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 2.1: Sharpless dihydroxylation / 7.1: Dess-Martin oxidation / 8.1: Wittig reaction / 8.2: Wittig reaction;
DOI:10.1002/anie.201102521

Reference yield:

: C₁₃H₂₀Cl₂O₄

: C₂₈H₅₃Cl₃O₆Si₂

: ((2S,3S)-3-((1R,2S,4S,5S,6S,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

: 1333237-05-0
((2S,3S)-3-((1R,2S,4S,5R,6R,9R,10S)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2,5,6-tetrachloroundecyl)oxiran-2-yl)methyl acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: diisobutylaluminium hydride / toluene / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

3.1: AD-mix-β; methanesulfonamide; water / tert-butyl alcohol / 46 h / 0 - 4 °C / Inert atmosphere

4.1: 1,4-diaza-bicyclo[2.2.2]octane; trifluoromethylsulfonic anhydride / dichloromethane / 19 h / -78 - 20 °C / Inert atmosphere

5.1: camphor-10-sulfonic acid / methanol / 2 h / 20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -15 °C / Inert atmosphere

7.1: pyridine; pyridine hydrofluoride / tetrahydrofuran / 15 h / 0 - 4 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C / Inert atmosphere

9.1: potassium hexamethylsilazane / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere

9.2: 1 h / -78 - 0 °C / Inert atmosphere

10.1: tetraethylammonium trichloride / dichloromethane / 1 h / -78 °C / Inert atmosphere

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; dmap; methanesulfonamide; pyridine hydrofluoride; trifluoromethylsulfonic anhydride; AD-mix-β; camphor-10-sulfonic acid; water; tetraethylammonium trichloride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; tert-butyl alcohol; 3.1: Sharpless dihydroxylation / 8.1: Dess-Martin oxidation / 9.1: Wittig reaction / 9.2: Wittig reaction;
DOI:10.1002/anie.201102521