(2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid

Base Information

• Chemical Name: (2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid
• CAS No.: 603130-13-8
• Molecular Formula: C11H19NO5
• Molecular Weight: 245.276
• DSSTox Substance ID: DTXSID70448490
• Wikidata: Q82267503
• Mol file: 603130-13-8.mol

Synonyms:603130-13-8;(2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid;(2S,5R)-5-BOC-AMINO-TETRAHYDROPYRAN-2-CARBOXYLIC ACID;(2S,5R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]oxane-2-carboxylic Acid;(2S,5R)-5-[(tert-butoxycarbonyl)amino]tetrahydro-2H-pyran-2-carboxylic acid;(2S,5R)-5-(tert-Butoxycarbonylamino)tetrahydro-2h-pyran-2-carboxylic acid;2,6-anhydro-5-[(tert-butoxycarbonyl)amino]-3,4,5-trideoxy-L-erythro-hexonic acid;(2S,5R)-5-{[(tert-butoxy)carbonyl]amino}oxane-2-carboxylic acid;(2S,5R)-5-(Boc-amino)tetrahydropyran-2-carboxylic acid;MFCD20261452;SCHEMBL4523657;DTXSID70448490;NROSRTMHTJHLLE-SFYZADRCSA-N;AMY12307;PB36003;AS-30023;CS-0039053;(2S,5R)-5-{[(Tert-butoxy)carbonyl]amino};A852652;(2S,5R)-5-{[(tert-butoxy)carbonyl]amino}oxane-2-;(2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylicacid;(2S,5R)-5-tert-butoxycarbonylamino-tetrahydro-pyran-2-carboxylic acid;(2S,5R)-5-(tert-butoxycarbonyl)-tetrahydro-2H-pyran-2-carboxylic acid

Chemical Property of (2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid

Chemical Property:

• Boiling Point: 413.9±45.0 °C(Predicted)
• PKA: 3.57±0.40(Predicted)
• PSA: 88.35000
• Density: 1.19±0.1 g/cm3(Predicted)
• LogP: 1.34770
• Storage Temp.: 2-8°C
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 245.12632271
• Heavy Atom Count: 17
• Complexity: 297

Purity/Quality:

97% ^*data from raw suppliers

(2S,5R)-5-[(tert-Butoxycarbonyl)amino]tetrahydro-2H-pyran-2-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1CCC(OC1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H]1CC[C@H](OC1)C(=O)O
• Uses: (2S,5R)-5-[(tert-Butoxycarbonyl)amino]tetrahydro-2H-pyran-2-carboxylic Acid is aids in the synthesis of novel tetrahydropyran-based, topoisomerase inhibitors with anti-gram-positive activity. Also used in the synthesis of novel tetrahydropyran-based dipeptide isoster compounds.

Technology Process of (2S,5R)-5-((tert-Butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid

There total 10 articles about (2S,5R)-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:

(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

Reference yield:

((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate (149342-25-6,92131-91-4) → (2S,5R)-5-((tert-butoxycarbonyl)amino)tetrahydro-2H-pyran-2-carboxylic acid (603130-13-8,1408074-42-9)

Guidance literature:

Multi-step reaction with 8 steps

1: tBuOK / methanol / 2 h

2: 8.3 g / pyridine / 0 °C

3: 76 percent / DBU / CH₂Cl₂ / 1 h / 0 °C

4: 89 percent / K₂CO₃ / 1,2-dichloro-benzene / 5 h / 180 °C

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

6: 1.5 g / CH₂Cl₂

7: 75 percent / H₂ / Pd/C / methanol / 16 h

8: 71 percent / NaIO₄ / RuCl₃*xH₂O / CH₂Cl₂; acetonitrile; H₂O / 3 h / 0 °C

With pyridine; potassium hydroxide; sodium periodate; potassium tert-butylate; 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; 4: 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

Downstream raw materials:

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

benzyl ((3R,6S)-6-(2-(3-fluoro-6-methoxy-1,5-naphthyridin-4-yl)acetyl)tetrahydro-2H-pyran-3-yl)carbamate

Methyl 2,6-anhydro-5-{[(benzyloxy)carbonyl]amino}-3,4,5-trideoxy-L-erythro-hexonate