tunicamycin V

Base Information

• Chemical Name: tunicamycin V
• CAS No.: 66054-36-2
• Molecular Formula: C₃₈H₆₂N₄O₁₆
• Molecular Weight: 830.927
• UNII: 17RV2Q5O9O
• DSSTox Substance ID: DTXSID601017533
• Nikkaji Number: J571.556C
• Wikidata: Q27133159
• Metabolomics Workbench ID: 63273
• ChEMBL ID: CHEMBL4534172
• Mol file: 66054-36-2.mol

Synonyms:tunicamycin B2

Chemical Property of tunicamycin V

Chemical Property:

• XLogP3: 0.2
• Hydrogen Bond Donor Count: 11
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 20
• Exact Mass: 830.41608190
• Heavy Atom Count: 58
• Complexity: 1420

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCCCCCCCC=CC(=O)NC1C(C(C(OC1OC2C(C(C(C(O2)CO)O)O)NC(=O)C)CC(C3C(C(C(O3)N4C=CC(=O)NC4=O)O)O)O)O)O
• Isomeric SMILES: CC(C)CCCCCCCCC/C=C/C(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@H]1O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)NC(=O)C)C[C@H]([C@@H]3[C@H]([C@H]([C@@H](O3)N4C=CC(=O)NC4=O)O)O)O)O)O

Technology Process of tunicamycin V

There total 76 articles about tunicamycin V 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: 97.0%

3-(benzyloxymethyl)-1-{(11S)-6,10-dideoxy-11-O-[2-acetamide-2-deoxy-4,6-O-isopropylidene-3-O-(methoxymethyl)-α-D-gluco-hexopyranosyl]-2,3:8,9-di-O-isopropylidene-5-O-(methoxymethyl)-10-(13-methyltetradec-2-enamido)-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl}uracil → tunicamycin V (66054-36-2)

Guidance literature:

3-(benzyloxymethyl)-1-{(11S)-6,10-dideoxy-11-O-[2-acetamide-2-deoxy-4,6-O-isopropylidene-3-O-(methoxymethyl)-α-D-gluco-hexopyranosyl]-2,3:8,9-di-O-isopropylidene-5-O-(methoxymethyl)-10-(13-methyltetradec-2-enamido)-L-galacto-β-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl}uracil; With boron trichloride; In dichloromethane; at -78 - 0 ℃; for 1h;

With sodium methylate; In methanol; dichloromethane; at 0 - 20 ℃; for 0.25h;

DOI:10.1021/acs.orglett.7b03623

Reference yield:

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside (147254-13-5) → tunicamycin V (66054-36-2)

Guidance literature:

Multi-step reaction with 21 steps

1: 87 percent / bromotrichloromethane / 2.5 h / 0 °C / Irradiation

2: 89 percent / diisopropylethylamine / CH₂Cl₂ / 15 h / Heating

3: 98 percent / triethylamine, benzeneselenol / 2.5 h / 60 °C

4: 1.) triethylamine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dichloromethane, 0 deg C, 10 min, 2.) toluene, 100 deg C, 1.5 h

5: 95 percent / triethylamine / 1,2-dimethoxy-ethane / 10 h / 90 °C

6: triethylamine trihydrofluoride / acetonitrile / 6 h / 23 °C

7: 1.) 4-A molecular sieves, 2.) trifluoromethanesulfonic acid / 1.) toluene, 23 deg C, 2 h, 2.) toluene, -20 deg C

8: 87 percent / hydrazine hydrate / ethanol / 12 h / 100 °C

9: 91 percent / pyridine / 0.5 h / 0 °C

10: 91 percent / benzeneselenol, triethylamine / 12 h / 55 °C

11: 91 percent / pyridine / 2.5 h / 60 °C

12: 1.) m-chloroperoxybenzoic acid, 2.) Me₂S, triethylamine / 1.) CCl₄, from -15 deg C to 0 deg C, 50 min, 2.) CCl₄, 65 deg C, 10 h

13: 92 percent / K₂CO₃ / methanol / 2 h / 23 °C

14: pyridine / toluene / 0.08 h / 23 °C

15: 85 percent / tributyltin hydride, bis(triphenylphosphine)palladium(II) chloride / CH₂Cl₂ / 0.1 h / 23 °C

16: triethylborane, tributyltin hydride / toluene; hexane / 0 °C

17: KF / methanol / 2 h / 23 °C

18: formic acid / Pd black / methanol / 1.5 h / 23 °C

19: formic acid / methanol / 5 h / 40 °C

20: 48percent aq. HF / methanol; acetonitrile / 2 h / 23 °C

21: 1.) 1,3-dicyclohexylcarbodiimide / 1.) CH₂Cl₂, 23 deg C, 20 min, 2.) MeOH, 23 deg C

With pyridine; potassium fluoride; formic acid; bis(triphenylphosphine)palladium(II)-chloride; dimethylsulfide; triethyl borane; Bromotrichloromethane; trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; hydrogen fluoride; tri-n-butyl-tin hydride; Benzeneselenol; potassium carbonate; hydrazine hydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; palladium; In methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00090a018

Reference yield:

C69H92N4O24SeSi2 → tunicamycin V (66054-36-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / tributyltin hydride, bis(triphenylphosphine)palladium(II) chloride / CH₂Cl₂ / 0.1 h / 23 °C

2: triethylborane, tributyltin hydride / toluene; hexane / 0 °C

3: KF / methanol / 2 h / 23 °C

4: formic acid / Pd black / methanol / 1.5 h / 23 °C

5: formic acid / methanol / 5 h / 40 °C

6: 48percent aq. HF / methanol; acetonitrile / 2 h / 23 °C

7: 1.) 1,3-dicyclohexylcarbodiimide / 1.) CH₂Cl₂, 23 deg C, 20 min, 2.) MeOH, 23 deg C

With potassium fluoride; formic acid; bis(triphenylphosphine)palladium(II)-chloride; triethyl borane; hydrogen fluoride; tri-n-butyl-tin hydride; dicyclohexyl-carbodiimide; palladium; In methanol; hexane; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00090a018

upstream raw materials:

(E)-13-methyl-2-tetradecenoic acid

C₂₃H₃₆N₄O₁₅

C₄₁H₆₆N₄O₁₆

1-<(11S)-11-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranosyl)-6,10-<(E)-13-methyl-2-tetradecenoyl>-amino-α-L-galacto-D-allo-undecodialdo-1,4-furanose-11,7-pyranos-1-yl>uracil