2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-threo-hexonic Acid

Base Information

• Chemical Name: 2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-threo-hexonic Acid
• CAS No.: 603130-25-2
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.276
• Mol file: 603130-25-2.mol

Synonyms:

Chemical Property of 2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-threo-hexonic Acid

Chemical Property:

• Boiling Point: 413.9±45.0 °C(Predicted)
• PKA: 3.57±0.40(Predicted)
• Density: 1.19±0.1 g/cm3(Predicted)

Purity/Quality:

≥95% ^*data from raw suppliers

2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-dimethylethoxy)carbonyl]amino]-D-threo-hexonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-dimethylethoxy)carbonyl]amino]-D-threo-hexonic Acid is used in the synthesis of tetrahydropyran-based dipeptide isoteres, with potential topoisomerase inhibitory activity.

Technology Process of 2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-threo-hexonic Acid

There total 11 articles about 2,6-Anhydro-3,4,5-trideoxy-5-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-threo-hexonic 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: 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,5S)-5-[(tert-butoxycarbonyl)amino]tetrahydropyran-2-carboxylic acid (603130-25-2,1408074-42-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 8.3 g / pyridine / 0 °C

2: 64 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / -30 - 20 °C

3: 76 percent / tBuOK / methanol / 16 h

4: 90 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

5: 76 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 180 °C

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

7: 2.4 g / CH₂Cl₂; propan-2-ol

8: 58 percent / H₂ / Pd/C / methanol / 16 h

9: 60 percent / NaIO₄ / RuCl₃*xH₂O / CH₂Cl₂; acetonitrile; H₂O / 0 °C

With pyridine; potassium hydroxide; sodium periodate; di-isopropyl azodicarboxylate; potassium tert-butylate; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; ruthenium trichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-benzene; isopropyl alcohol; acetonitrile; 2: Mitsunobu epimerization / 5: Overman rearrangement;

DOI:10.1002/ejoc.200200710

Reference yield:

((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4) → (2S,5S)-5-[(tert-butoxycarbonyl)amino]tetrahydropyran-2-carboxylic acid (603130-25-2,1408074-42-9)

Guidance literature:

Multi-step reaction with 10 steps

1: tBuOK / methanol / 2 h

2: 8.3 g / pyridine / 0 °C

3: 64 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / -30 - 20 °C

4: 76 percent / tBuOK / methanol / 16 h

5: 90 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

6: 76 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 180 °C

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

8: 2.4 g / CH₂Cl₂; propan-2-ol

9: 58 percent / H₂ / Pd/C / methanol / 16 h

10: 60 percent / NaIO₄ / RuCl₃*xH₂O / CH₂Cl₂; acetonitrile; H₂O / 0 °C

With pyridine; potassium hydroxide; sodium periodate; di-isopropyl azodicarboxylate; potassium tert-butylate; hydrogen; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; ruthenium trichloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-benzene; isopropyl alcohol; acetonitrile; 3: Mitsunobu epimerization / 6: Overman rearrangement;

DOI:10.1002/ejoc.200200710

upstream raw materials:

((3S,6S)-6-Hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

(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

Downstream raw materials:

(2S,5S)-5-Amino-tetrahydro-pyran-2-carboxylic acid

Refernces