2H-Pyran-2-one, 6-(3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrienyl)-5-ethyl-5,6-dihydro-

Base Information

• Chemical Name: 2H-Pyran-2-one, 6-(3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrienyl)-5-ethyl-5,6-dihydro-
• CAS No.: 124123-09-7
• Molecular Formula: C₂₅H₄₀NO₈P
• Molecular Weight: 513.568
• Nikkaji Number: J410.809D
• Wikipedia: Phoslactomycin_B
• Mol file: 124123-09-7.mol

Synonyms:phoslactomycin B

Chemical Property of 2H-Pyran-2-one, 6-(3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrienyl)-5-ethyl-5,6-dihydro-

Chemical Property:

• Boiling Point: 753.1°Cat760mmHg
• Flash Point: 409.3°C
• PSA: 34.14000
• Density: 1.309g/cm³
• LogP: 1.52860
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 513.24915423
• Heavy Atom Count: 35
• Complexity: 829

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCCC2)O)OP(=O)(O)O)O
• Isomeric SMILES: CCC1C=CC(=O)OC1/C=C/C(CCN)(C(CC(/C=C/C=C/C2CCCCC2)O)OP(=O)(O)O)O

Technology Process of 2H-Pyran-2-one, 6-(3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrienyl)-5-ethyl-5,6-dihydro-

There total 16 articles about 2H-Pyran-2-one, 6-(3-(2-aminoethyl)-10-cyclohexyl-3,6-dihydroxy-4-(phosphonooxy)-1,7,9-decatrienyl)-5-ethyl-5,6-dihydro- 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: 88.0%

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one (902782-26-7) → (+)-phoslactomycin B (122856-26-2,124123-09-7)

Guidance literature:

With water; tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1002/anie.200600458

Reference yield: 73.0%

allyl {(3R,4R,6R,7Z,9Z)-4-{[bis(allyloxy)phosphoryl]oxy}-10-cyclohexyl-3-{(E)-2-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]vinyl}-3,6-dihydroxydeca-7,9-dien-1-yl}carbamate (1030827-29-2) → (+)-phoslactomycin B (122856-26-2,124123-09-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; water; tri-n-butyl-tin hydride; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ol8004672

Reference yield:

(2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-[2-(tert-butyldiphenylsiloxy)ethyl]-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynal (902782-38-1) → (+)-phoslactomycin B (122856-26-2,124123-09-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 2.40 g / Bu₄NOH / tetrahydrofuran; methanol / 6 h / -18 °C

2: 86 percent / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 20 °C

3: 94 percent / Ti(O-iPr)4 / benzene / 0.33 h / 80 °C

4: 88 percent / Bu₄NF / tetrahydrofuran / 0.83 h / 0 - 20 °C

5: 83 percent / Zn; dibromoethane; LiBr / CuBr / ethanol; tetrahydrofuran / 2 h / 80 °C

6: 85 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

7: 2,6-lutidine / CH₂Cl₂ / 0.33 h / 0 °C

8: 558 mg / pyridinium p-toluenesulfonate / methanol; tetrahydrofuran / 4 h / 0 °C

9: 73 percent / PPh₃; diisopropyl azodicarboxylate / toluene / -78 - 0 °C

10: 85 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; H₂O / 30 h / 0 °C

11: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

12: 311 mg / H₂O₂ / CH₂Cl₂ / 2 h / 0 °C

13: 95 percent / AcCl / methanol; tetrahydrofuran; CH₂Cl₂ / 2.5 h / 0 °C

14: 88 percent / Bu₃SnH; H₂O / PdCl₂(PPh₃)2 / CH₂Cl₂ / 1.5 h / 0 °C

With pyridine; 2,6-dimethylpyridine; 1H-tetrazole; titanium(IV) isopropylate; 1,1-Dibromoethane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; dihydrogen peroxide; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; acetyl chloride; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; zinc; bis-triphenylphosphine-palladium(II) chloride; copper(I) bromide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; toluene; benzene;

DOI:10.1002/anie.200600458

upstream raw materials:

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-(2-(bis(allyloxycarbonyl)amino)ethyl)-10-cyclohexyl-4-(diallyloxyphosphinyl)-3,6-dihydroxydeca-1,7,9-trienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

ethyl (2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-(2-(tert-butyldiphenylsiloxy)ethyl)-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynethioate

(2R,3S,4E,6R,7R,9R,12Z)-9-(tert-butyldimethylsiloxy)-6-[2-(tert-butyldiphenylsiloxy)ethyl]-13-cyclohexyl-2-ethyl-7-(4-methoxybenzyloxy)-3,6-bis(triethylsiloxy)trideca-4,12-dien-10-ynal

ethyl (2Z,4S,5S,6E,8R,9R,11R,14Z)-11-(tert-butyldimethylsiloxy)-8-[2-(tert-butyldiphenylsiloxy)ethyl]-15-cyclohexyl-4-ethyl-9-(4-methoxybenzyloxy)-5,8-bis(triethylsiloxy)pentadeca-2,6,14-trien-12-ynoate

Refernces

• 1、 Shibahara, Setsuya,Fujino, Masataka,Tashiro, Yasumasa,Takahashi, Keisuke,Ishihara, Jun,Hatakeyama, Susumi. "Asymmetric total synthesis of (+)-phoslactomycin B". supporting information; experimental part. p. 2139 - 2142. Retrieved 2009/07/04.