Streptothricin F

Base Information

• Chemical Name: Streptothricin F
• CAS No.: 3808-42-2
• Molecular Formula: C₁₉H₃₄N₈O₈
• Molecular Weight: 502.528
• DSSTox Substance ID: DTXSID20191489
• Nikkaji Number: J62.611B
• Wikidata: Q27128676
• Metabolomics Workbench ID: 144027
• ChEMBL ID: CHEMBL4448608
• Mol file: 3808-42-2.mol

Synonyms:racemomycin A;S15-1-A;streptothricin F;yazumycin A

Chemical Property of Streptothricin F

Chemical Property:

• Refractive Index: 1.6910 (estimate)
• Boiling Point: 592.64°C (rough estimate)
• PKA: 12.66±0.70(Predicted)
• PSA: 268.90000
• Density: 1.91g/cm³
• LogP: -2.27560
• XLogP3: -5.5
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 11
• Exact Mass: 502.24996007
• Heavy Atom Count: 35
• Complexity: 816

Purity/Quality:

99% ^*data from raw suppliers

STREPTOTHRICIN F 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCN)N)O
• Isomeric SMILES: C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCN)N)O

Technology Process of Streptothricin F

There total 13 articles about Streptothricin F 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:

(3R,4S,5R,6R)-2-Allyloxy-3-amino-6-hydroxymethyl-5-(2-methoxy-ethoxymethoxy)-tetrahydro-pyran-4-ol (83663-05-2) → streptothricin F (3808-42-2,67392-16-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

2: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

3: ZnBr₂ / CH₂Cl₂

4: Zn(powder) / methanol / 3 h / Ambient temperature

5: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

6: 95 percent / pyridine

7: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

8: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

9: 68 percent

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; mercury dichloride; mercury(II) oxide; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

Reference yield:

allyl 6-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-D-gulopyranoside (83663-04-1) → streptothricin F (3808-42-2,67392-16-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 73 percent / ethyldiisopropylamine / dioxane / 4 h / 70 °C

2: Ba(OH)2 / ethanol; H₂O / 1 h / Heating

3: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

4: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

5: ZnBr₂ / CH₂Cl₂

6: Zn(powder) / methanol / 3 h / Ambient temperature

7: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

8: 95 percent / pyridine

9: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

10: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

11: 68 percent

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

Reference yield:

Acetic acid (1R,2R,4S,5R,6R)-4-allyloxy-5-benzyloxycarbonylamino-3,7-dioxa-bicyclo[4.1.0]hept-2-ylmethyl ester → streptothricin F (3808-42-2,67392-16-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 100 percent / 2.) H₂O / acetic acid

2: 73 percent / ethyldiisopropylamine / dioxane / 4 h / 70 °C

3: Ba(OH)2 / ethanol; H₂O / 1 h / Heating

4: 91 percent / EtOCOCl, triethylamine / tetrahydrofuran

5: 66 percent / BaO-Ba(OH)2 / dimethylformamide / 15 h / Ambient temperature

6: ZnBr₂ / CH₂Cl₂

7: Zn(powder) / methanol / 3 h / Ambient temperature

8: 1.) RhCl(PPh₃)3; 2.) HgCl₂-HgO

9: 95 percent / pyridine

10: HBr / CH₂Cl₂ / 0.5 h / Ambient temperature

11: CaSO₄ / 1.) CH₂Cl₂, room temp., 30 min.; 2.) acetone

12: 68 percent

With pyridine; calcium sulfate; barium dihydroxide; RhCl(PPh₃)3; water; hydrogen bromide; chloroformic acid ethyl ester; triethylamine; N-ethyl-N,N-diisopropylamine; mercury dichloride; mercury(II) oxide; barium(II) oxide; zinc dibromide; zinc; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)87506-1

upstream raw materials:

C₆₂H₇₆N₈O₁₅S

(3R,4S,5R,6R)-2-Allyloxy-3-amino-6-hydroxymethyl-5-(2-methoxy-ethoxymethoxy)-tetrahydro-pyran-4-ol

allyl 6-O-acetyl-2-amino-2-N,3-O-carbonyl-2-deoxy-α-D-gulopyranoside

Acetic acid (3aR,4S,6R,7R,7aS)-4-allyloxy-7-(2-methoxy-ethoxymethoxy)-2-oxo-hexahydro-pyrano[3,4-d]oxazol-6-ylmethyl ester

Refernces