5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid

Base Information

• Chemical Name: 5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid
• CAS No.: 1408074-42-9
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.276
• Mol file: 1408074-42-9.mol

Synonyms:5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid;5-{[(tert-butoxy)carbonyl]amino}oxane-2-carboxylic acid

Chemical Property of 5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid

Chemical Property:

• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic Acid

Technology Process of 5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid

There total 33 articles about 5-((tert-Butoxycarbonyl)aMino)tetrahydro-2H-pyran-2-carboxylic Acid 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: 78.0%

1,5-anhydro-2-[(tert-butoxycarbonyl)amino]-2,3,4-trideoxy-D-erythro-hexitol (603130-12-7) → (2S,5R)-5-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid (603130-13-8,1408074-42-9)

Guidance literature:

1,5-anhydro-2-[(tert-butoxycarbonyl)amino]-2,3,4-trideoxy-D-erythro-hexitol; With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; Aliquat 336; sodium hydrogencarbonate; potassium bromide; In Isopropyl acetate; at 0 - 10 ℃; for 1.5h;

at 5 - 10 ℃; for 1.5h;

Reference yield: 60.0%

((3S,6S)-6-Hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (603130-24-1) → (2S,5S)-5-[(tert-butoxycarbonyl)amino]tetrahydropyran-2-carboxylic acid (603130-25-2,1408074-42-9)

Guidance literature:

With sodium periodate; ruthenium trichloride; In dichloromethane; water; acetonitrile; at 0 ℃;

DOI:10.1002/ejoc.200200710

Reference yield:

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol (125901-90-8) → (2S,5R)-5-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid (603130-13-8,1408074-42-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 8.3 g / pyridine / 0 °C

2: 76 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

3: 89 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 180 °C

4: KOH / propan-2-ol / 72 h

5: 1.5 g / CH₂Cl₂

6: 75 percent / H₂ / Pd/C / methanol / 16 h

7: 71 percent / NaIO₄ / RuCl₃*xH₂O / CH₂Cl₂; acetonitrile; H₂O / 3 h / 0 °C

With pyridine; potassium hydroxide; sodium periodate; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; ruthenium trichloride; palladium on activated charcoal; In methanol; dichloromethane; water; 1,2-dichloro-benzene; isopropyl alcohol; acetonitrile; 3: Overman rearrangement;

DOI:10.1002/ejoc.200200710

upstream raw materials:

1,5-anhydro-2-[(tert-butoxycarbonyl)amino]-2,3,4-trideoxy-D-erythro-hexitol

(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

6-O-(tert-butyldimethylsilyl)-1,5-anhydro-2,3-dideoxy-D-erythro-hex-2-enitol

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