((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

Base Information

• Chemical Name: ((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
• CAS No.: 1333237-02-7
• Molecular Formula: C₃₅H₆₀Cl₂O₆Si₂
• Molecular Weight: 703.935
• Mol file: 1333237-02-7.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 20 articles about ((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 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: 55.0%

C16H28Cl2O5Si (1333237-04-9) + ((4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)hexyl)triphenylphosphonium iodide (1333237-00-5) → C35H59ClO6Si2 (1333237-65-2) + ((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 (1333237-02-7)

Guidance literature:

((4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)hexyl)triphenylphosphonium iodide; With potassium hexamethylsilazane; In tetrahydrofuran; at 0 ℃; for 0.333333h; Inert atmosphere;

C₁₆H₂₈Cl₂O₅Si; In tetrahydrofuran; at -78 - 0 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

(4R,5S,E)-4,5-dichloro-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)hex-2-en-1-ol (1333236-45-5) → C35H59ClO6Si2 (1333237-65-2) + ((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 (1333237-02-7)

Guidance literature:

Multi-step reaction with 8 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

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; 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 → C35H59ClO6Si2 (1333237-65-2) + ((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 (1333237-02-7)

Guidance literature:

Multi-step reaction with 9 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

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; 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

upstream raw materials:

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

(4R,5S,e)-4,5-dichloro-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)hex-2-enyl acetate

(2R,3S,4R,5S)-4,5-dichloro-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,3-dihydroxyhexyl acetate

((2S,3S)-3-((1R,2S)-1,2-dichloro-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)propyl)oxiran-2-yl)methyl acetate

Downstream raw materials:

((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