(3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate

Base Information

• Chemical Name: (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate
• CAS No.: 1345017-54-0
• Molecular Formula: C₃₁H₄₇NO₇Si
• Molecular Weight: 573.802

Synonyms:(3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate

Chemical Property of (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate

There total 7 articles about (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl 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:

(3S,7R,E)-7-(tert-butoxycarbonylamino)-8-(tert-butyldiphenylsilyloxy)oct-5-en-3-yl acetate (1345017-52-8) → (3S,5S,6S,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate (1345017-53-9) + (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate (1345017-54-0)

Guidance literature:

With potassium osmate(VI) dihydrate; methanesulfonamide; AD-mix-α; water; sodium hydrogencarbonate; hydroquinidein 1,4-phthalazinediyl diether; In tert-butyl alcohol; at 0 ℃; for 24h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

tert-butyl (2S,3R)-3-(allyloxy)-1-hydroxypent-4-en-2-ylcarbamate (1345017-48-2) → (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate (1345017-54-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

3.1: sodium tetrahydroborate; cobalt(III) chloride hexahydrate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

4.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: osmium(VIII) oxide; methanesulfonamide; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide / acetone; toluene / 12 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; methanesulfonamide; cobalt(III) chloride hexahydrate; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone; toluene; 2.1: Wittig rearrangement;

DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

(S)-tert-butyl 4-((R)-1-(allyloxy)allyl)-2,2-dimethyloxazolidine-3-carboxylate (1345017-47-1) → (3S,5R,6R,7S)-7-((tert-butoxycarbonyl)amino)-8-((tert-butyldiphenylsilyl)oxy)-5,6-dihydroxyoctan-3-yl acetate (1345017-54-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate; cobalt(III) chloride hexahydrate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: osmium(VIII) oxide; methanesulfonamide; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide / acetone; toluene / 12 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; methanesulfonamide; cobalt(III) chloride hexahydrate; water; sodium hydrogencarbonate; acetic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; 3.1: Wittig rearrangement;

DOI:10.1016/j.tetlet.2011.08.084

upstream raw materials:

(S)-tert-butyl 4-((R)-1-(allyloxy)allyl)-2,2-dimethyloxazolidine-3-carboxylate

tert-butyl (2S,3R)-3-(allyloxy)-1-hydroxypent-4-en-2-ylcarbamate

tert-butyl (2S,3R)-3-(allyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate

tert-butyl (2R,6R,E)-1-(tert-butyldiphenylsilyloxy)-6-hydroxyocta-3,7-dien-2-ylcarbamate

Downstream raw materials:

tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

(3aR,4S,6R,7aR)-tert-butyl-4-((tert-butyldiphenylsilyloxy)methyl)-6-ethyl-2,2-dimethyltetrahydro-[1,3]dioxolo[4,5-c]pyridine-5(6H)-carboxylate

(S)-1-((4R,5R)-2,2-dimethyl-5-((S)-2,2,10,10-tetramethyl-8-oxo-3,3-diphenyl-4,9-dioxa-7-aza-3-silaundecan-6-yl)-1,3-dioxolan-4-yl)butan-2-yl acetate

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