(2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine

Base Information

• Chemical Name: (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine
• CAS No.: 1438280-08-0
• Molecular Formula: C₂₇H₄₇NO₄SSi₂
• Molecular Weight: 537.911

Synonyms:(2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine

Chemical Property of (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine

There total 5 articles about (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine 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:

(2S,3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(pentyloxy)-1-tosylpiperidine (1438279-88-9) + allenyltributylstannane (53915-69-8) → (2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438279-90-3) + (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438280-08-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 0.0833333h; Overall yield = 97 %; Overall yield = 52.2 mg; Inert atmosphere;

DOI:10.1002/anie.201206967

Reference yield:

(S)-N-(but-3-en-1-yl)-4-methyl-N-(1-(pentyloxy)allyl)benzenesulfonamide (1438280-00-2) → (2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438279-90-3) + (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438280-08-0)

Guidance literature:

Multi-step reaction with 4 steps

1: Grubbs catalyst first generation / dichloromethane / 1 h / 20 °C / Inert atmosphere

2: 4-methyl-2-morpholinone; osmium(VIII) oxide / acetone; tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

3: 1H-imidazole; dmap / dichloromethane; N,N-dimethyl-formamide / Inert atmosphere

4: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; 4-methyl-2-morpholinone; dmap; osmium(VIII) oxide; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.201206967

Reference yield:

N-tosyl-3-butenylamine (10285-80-0) → (2R,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438279-90-3) + (2S,3S,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(prop-2-ynyl)-1-tosylpiperidine (1438280-08-0)

Guidance literature:

Multi-step reaction with 5 steps

1: (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); palladium diacetate; triethylamine / dichloromethane / 18 h / 20 °C / Inert atmosphere

2: Grubbs catalyst first generation / dichloromethane / 1 h / 20 °C / Inert atmosphere

3: 4-methyl-2-morpholinone; osmium(VIII) oxide / acetone; tetrahydrofuran; water / 0 - 20 °C / Inert atmosphere

4: 1H-imidazole; dmap / dichloromethane; N,N-dimethyl-formamide / Inert atmosphere

5: boron trifluoride diethyl etherate / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

With 1H-imidazole; Grubbs catalyst first generation; 4-methyl-2-morpholinone; dmap; osmium(VIII) oxide; boron trifluoride diethyl etherate; palladium diacetate; triethylamine; (1R,2R)-(+)-1,2-diaminocyclohexane-N,N’-bis(2-diphenylphosphino-1-naphthoyl); In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/anie.201206967

upstream raw materials:

(S)-6-(pentyloxy)-1-tosyl-1,2,3,6-tetrahydropyridine

(2S,3R,4R)-2-(pentyloxy)-1-tosylpiperidine-3,4-diol

(2S,3R,4R)-3,4-bis(tert-butyldimethylsilyloxy)-2-(pentyloxy)-1-tosylpiperidine

allenyltributylstannane

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