beta-ERYTHROIDINE

Base Information

• Chemical Name: beta-ERYTHROIDINE
• CAS No.: 466-81-9
• Molecular Formula: C₁₆H₁₉NO₃
• Molecular Weight: 273.332
• European Community (EC) Number: 684-444-6
• UNII: 7334EOU8K5
• DSSTox Substance ID: DTXSID30196884
• Nikkaji Number: J5.901C
• Wikidata: Q27103335
• Metabolomics Workbench ID: 67583
• ChEMBL ID: CHEMBL3318888
• Mol file: 466-81-9.mol

Synonyms:beta-erythroidine;beta-erythroidine hydrobromide;beta-erythroidine hydrochloride;beta-erythroidine hydrochloride, hemihydrate;beta-erythroidine hydroiodide;beta-erythroidine perchlorate;beta-erythroidine sodium salt

Chemical Property of beta-ERYTHROIDINE

Chemical Property:

• Vapor Pressure: 8.54E-11mmHg at 25°C
• Melting Point: 99.5-100°
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 517°Cat760mmHg
• PKA: 5.85±0.40(Predicted)
• Flash Point: 266.5°C
• PSA: 38.77000
• Density: 1.27g/cm³
• LogP: 1.52720
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 273.13649347
• Heavy Atom Count: 20
• Complexity: 560

Purity/Quality:

99% ^*data from raw suppliers

BETA-ERYTHROIDINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1CC23C4=C(CCN2CC=C3C=C1)COC(=O)C4
• Isomeric SMILES: CO[C@@H]1C[C@]23C4=C(CCN2CC=C3C=C1)COC(=O)C4
• Uses: [2R-(2R*,13bS*)]-2,6,8,9,10,13-Hexahydro-2-methoxy-1H,12H-benzo[i]pyrano[3,4-g]indolizin-12-one,

Technology Process of beta-ERYTHROIDINE

There total 15 articles about beta-ERYTHROIDINE 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:

methyl (2S,4R)-2-amino-2-ethynyl-4-methoxyhex-5-enoate (896744-74-4) → β-erythroidine (466-81-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / sodium triacetoxyborohydride; molecular sieves 4 Angstroem / tetrahydrofuran / 9 h / 20 °C

2: 97 percent / K₂CO₃ / dimethylformamide / 21 h / 100 °C

3: 84 percent / NaH; methanol / toluene; various solvent(s) / 0.5 h / Heating; Dieckmann condensation

4: NaH; AlH₃ / various solvent(s); tetrahydrofuran / 3 h / 0 °C

5: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

6: 246.0 mg / SmI₂ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; aluminium hydride; methanol; samarium diiodide; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Reformatsky reaction;

DOI:10.1002/anie.200600210

Reference yield:

((1S,3R)-1-Ethynyl-1-formyl-3-methoxy-pent-4-enyl)-carbamic acid tert-butyl ester → β-erythroidine (466-81-9)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH₂PO₄*2H₂O; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 9 h / 20 °C

2: CH₂Cl₂; diethyl ether / 3 h / 20 °C

3: 1.1 g / trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

4: 86 percent / sodium triacetoxyborohydride; molecular sieves 4 Angstroem / tetrahydrofuran / 9 h / 20 °C

5: 97 percent / K₂CO₃ / dimethylformamide / 21 h / 100 °C

6: 84 percent / NaH; methanol / toluene; various solvent(s) / 0.5 h / Heating; Dieckmann condensation

7: NaH; AlH₃ / various solvent(s); tetrahydrofuran / 3 h / 0 °C

8: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

9: 246.0 mg / SmI₂ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; aluminium hydride; methanol; sodium chlorite; sodium dihydrogenphosphate; samarium diiodide; 2-methyl-but-2-ene; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1: Pinnick oxidation / 9: Reformatsky reaction;

DOI:10.1002/anie.200600210

Reference yield:

(2S,4R)-2-tert-Butoxycarbonylamino-2-ethynyl-4-methoxy-hex-5-enoic acid → β-erythroidine (466-81-9)

Guidance literature:

Multi-step reaction with 9 steps

1: CH₂Cl₂; diethyl ether / 3 h / 20 °C

2: 1.1 g / trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

3: 86 percent / sodium triacetoxyborohydride; molecular sieves 4 Angstroem / tetrahydrofuran / 9 h / 20 °C

4: 97 percent / K₂CO₃ / dimethylformamide / 21 h / 100 °C

5: 84 percent / NaH; methanol / toluene; various solvent(s) / 0.5 h / Heating; Dieckmann condensation

6: NaH; AlH₃ / various solvent(s); tetrahydrofuran / 3 h / 0 °C

7: pyridine / CH₂Cl₂ / 0.25 h / 0 °C

8: 246.0 mg / SmI₂ / tetrahydrofuran / 0.5 h / 0 °C

With pyridine; aluminium hydride; methanol; samarium diiodide; 4 A molecular sieve; sodium tris(acetoxy)borohydride; sodium hydride; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 8: Reformatsky reaction;

DOI:10.1002/anie.200600210

upstream raw materials:

α-erythroidine

(5S)-6-allyl-5-ethynyl-hexahydro-4a-hydroxy-5-((R)-2-methoxybut-3-enyl)-1H-pyrano[4,3-c]pyridin-3(4H)-one

methyl (2S,4R)-2-amino-2-ethynyl-4-methoxyhex-5-enoate

(4S,5R)-2-(trichloromethyl)-4-ethynyl-5,6-dihydro-4-((R)-2-methoxybut-3-enyl)-4H-1,3-oxazin-5-ol

Downstream raw materials:

β-Erythroidinol

Refernces