Hygromycin A

Base Information

• Chemical Name: Hygromycin A
• CAS No.: 6379-56-2
• Deprecated CAS: 102489-39-4,11049-00-6
• Molecular Formula: C₂₃H₂₉NO₁₂
• Molecular Weight: 511.483
• UNII: 3YJY415DDI
• Nikkaji Number: J152.079B
• Wikipedia: Totomycin
• Wikidata: Q27137757
• Metabolomics Workbench ID: 117718
• ChEMBL ID: CHEMBL267436
• Mol file: 6379-56-2.mol

Synonyms:hygromycin;hygromycin A

Chemical Property of Hygromycin A

Chemical Property:

• Melting Point: 105-109°; mp 110-112° (dec) (Chida)
• PKA: 8.9(at 25℃)
• PSA: 207.96000
• LogP: -1.62710
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 6
• Exact Mass: 511.16897536
• Heavy Atom Count: 36
• Complexity: 853

Purity/Quality:

99%, ^*data from raw suppliers

HYGROMYCIN A 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC1=CC(=C(C=C1)OC2C(C(C(O2)C(=O)C)O)O)O)C(=O)NC3C(C(C4C(C3O)OCO4)O)O
• Isomeric SMILES: C/C(=C\C1=CC(=C(C=C1)O[C@H]2[C@H]([C@@H]([C@H](O2)C(=O)C)O)O)O)/C(=O)N[C@@H]3[C@@H]([C@H]([C@@H]4[C@H]([C@@H]3O)OCO4)O)O
• Uses: Hygromycin A, a neglected antibiotic,?selectively kills the bacteria that cause Lyme disease. It?was able to treat Lyme disease in mice without disrupting the microbiome. Medicine (broad-spectrum antibiotic).

Technology Process of Hygromycin A

There total 30 articles about Hygromycin A 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: 98.0%

(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide (1410798-42-3) → hygromycin A (75081-92-4,6379-56-2,11049-00-6,102489-39-4)

Guidance literature:

(-)-(2E)-3-(4-{[6-deoxy-2,3-bis-O-(triisopropylsilyl)-β-D-arabino-hexofuranosyl-5-ulose]oxy}-3-hydroxphenyl)-2-methyl-N-[(3aS,4R,5R,6S,7R,7aR)-4,6,7-trihydroxyhexahydro-1,3-benzodioxol-5-yl] acrylamide; With tris(dimethylamino)sulfonium trimethylsilyldifluoride; In N,N-dimethyl-formamide; at 0 ℃; for 4.5h;

With trifluoroacetic acid; In N,N-dimethyl-formamide; pH=2;

DOI:10.1002/anie.200902840

Reference yield: 45.0%

hygromycin A ethylene acetal (127213-11-0) → hygromycin A (75081-92-4,6379-56-2,11049-00-6,102489-39-4)

Guidance literature:

With trifluoroacetic acid; In water; for 1h; Ambient temperature;

DOI:10.1021/jo00009a009

Reference yield:

methyl 2,3-di-O-benzyl-α-D-altropyranoside (33164-03-3) → hygromycin A (75081-92-4,6379-56-2,11049-00-6,102489-39-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 74 percent / diethyl azodicarboxylate, triphenylphosphine, CH₃I / tetrahydrofuran / 19 h / Ambient temperature

2: DBU / toluene / 23 h / 80 °C

3: Amberlite IR 120 B resin / tetrahydrofuran; H₂O / 22 h / Ambient temperature

4: 77 percent / diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 2.5 h / Ambient temperature

5: 46 percent / H₂ / Pd(OH)2/C / ethyl acetate / 0.5 h / 760 Torr / Ambient temperature

6: 96 percent / pyridine / Ambient temperature

7: 86 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 8 h / -5 °C

8: 66 percent / ceric ammonium nitrate / acetonitrile; H₂O / 14 h / 5 °C

9: 94 percent / CH₂Cl₂ / 14 h / Ambient temperature

10: 1.) 1M aq. NaOH, 2.) pyridine / 1.) MeOH, 50 deg C, overnight, 2.) overnight

11: 1.) diethyl cyanophosphonate, NEt₃, 2.) pyridine / 1.) DMF, 0 deg C, 2.5 h, 2.) RT, 2 h

12: 94 percent / NaOMe / methanol / 0.5 h / 0 °C

13: 45 percent / trifluoroacetic acid / H₂O / 1 h / Ambient temperature

With pyridine; sodium hydroxide; ammonium cerium(IV) nitrate; diethyl cyanophosphonate; trimethylsilyl trifluoromethanesulfonate; Amberlite IR 120 B resin; hydrogen; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; methyl iodide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo00009a009

upstream raw materials:

hygromycin A ethylene acetal

Acetic acid (2S,3S,4S,5S)-4-acetoxy-5-{2-acetoxy-4-[(E)-2-((3aS,4R,5S,6S,7R,7aS)-4,6,7-triacetoxy-hexahydro-benzo[1,3]dioxol-5-ylcarbamoyl)-propenyl]-phenoxy}-2-(2-methyl-[1,3]dioxolan-2-yl)-tetrahydro-furan-3-yl ester

2-acetoxy-4-<(E)-2-carboxy-1-propen-1-yl>phenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

2-acetoxy-4-methylphenyl 2',3'-di-O-acetyl-6'-deoxy-β-D-arabino-5'-hexulofuranoside ethylene acetal

Downstream raw materials:

Hygromycin-hexaacetat

Refernces

• 1、 Donohoe, Timothy J.,Flores, Aida,Bataille, Carole J. R.,Churruca, Fatima. "Synthesis of (-)-hygromycin a: application of Mitsunobu glycosylation and tethered aminohydroxylation". supporting information; experimental part. p. 6507 - 6510. Retrieved 2009/12/06.
• 2、 Chida, Noritaka,Ohtsuka, Masami,Nakazawa, Keiichi,Ogawa, Seiichiro. "Total Synthesis of Hygromycin A". . p. 436 - 438. Retrieved 2007/10/02.