methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate

Base Information

Chemical Name:methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate
CAS No.:114582-75-1
Molecular Formula:C₂₂H₃₂N₂O₃S
Molecular Weight:404.574
Hs Code.:
ChEMBL ID:CHEMBL490508
Nikkaji Number:J1.011.165J
Wikidata:Q105309711

Synonyms:CHEMBL490508

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Chemical Property of methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate

Chemical Property:

Vapor Pressure:2.81E-13mmHg at 25°C
Boiling Point:557.8°C at 760 mmHg
Flash Point:291.1°C
Density:1.082g/cm³
XLogP3:5.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:13
Exact Mass:404.21336406
Heavy Atom Count:28
Complexity:572

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC(C)(C1=NC(=CS1)CC=CCC=C)C(CC=CC(=C)CCNC(=O)OC)O
Isomeric SMILES:CC(C)(C1=NC(=CS1)C/C=C\CC=C)[C@@H](C/C=C\C(=C)CCNC(=O)OC)O

Technology Process of methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate

There total 22 articles about methyl N-[(Z,7R)-8-[4-[(2Z)-hexa-2,5-dienyl]-1,3-thiazol-2-yl]-7-hydroxy-8-methyl-3-methylidenenon-4-enyl]carbamate 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: 33.0%

: 912542-61-1
(Z)-2-[((E)-4-Hexa-2,5-dienyl)-thiazol-2-yl]-9-isocyanato-2-methyl-7-methylene-non-5-en-3-ol

: 67-56-1
methanol

: 114582-75-1
mycothiazole

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tet.2006.07.010

Reference yield:

: 845660-05-1
2-{2-[(tert-butyldimethylsilyl)oxy]-1,1-dimethylpent-4-enyl}thiazole-4-carboxaldehyde

: 114582-75-1
mycothiazole

Guidance literature:: Multi-step reaction with 13 steps

1.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C

2.1: 97 percent / 2,6-lutidine; PPh₃; CBr₄ / acetonitrile / 0.5 h / 20 °C

3.1: 95 percent / N-methylpyrrolidinone / PdCl₂(CH₃CN)2 / 0.5 h / 20 °C

4.1: 94 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 50 °C

5.1: DMAP / tetrahydrofuran / 1 h / 20 °C

6.1: 98 mg / second generation Grubbs' catalyst / benzene / 1 h / 70 °C

7.1: 76 percent / HMPA; LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 60 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

9.1: PPTS / tetrahydrofuran; H₂O / 18 h / 50 °C

10.1: NaClO₂; NaH₂PO₄*H₂O; 2-methyl-but-2-ene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

11.1: diphenylphosphoryl azide; Et₃N / toluene / 1 h / 20 °C

12.1: 10 mg / 1 h / 110 °C

13.1: 33 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; carbon tetrabromide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; benzene; 3.1: Stille coupling reaction / 12.1: Curtius rearrangement;
DOI:10.1016/j.tet.2006.07.010

Reference yield:

: 845660-03-9
4-bromo-2-{2-[(tert-butyldimethylsilyl)oxy]-1,1-dimethylpent-4-enyl}thiazole

: 114582-75-1
mycothiazole

Guidance literature:: Multi-step reaction with 14 steps

1.1: t-BuLi / pentane; diethyl ether / 0.08 h / -78 °C

1.2: 85 percent / pentane; diethyl ether / 0.5 h / -78 °C

2.1: DIBAL-H / diethyl ether; hexane / 0.5 h / -78 °C

3.1: 97 percent / 2,6-lutidine; PPh₃; CBr₄ / acetonitrile / 0.5 h / 20 °C

4.1: 95 percent / N-methylpyrrolidinone / PdCl₂(CH₃CN)2 / 0.5 h / 20 °C

5.1: 94 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 50 °C

6.1: DMAP / tetrahydrofuran / 1 h / 20 °C

7.1: 98 mg / second generation Grubbs' catalyst / benzene / 1 h / 70 °C

8.1: 76 percent / HMPA; LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

9.2: 60 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C

10.1: PPTS / tetrahydrofuran; H₂O / 18 h / 50 °C

11.1: NaClO₂; NaH₂PO₄*H₂O; 2-methyl-but-2-ene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

12.1: diphenylphosphoryl azide; Et₃N / toluene / 1 h / 20 °C

13.1: 10 mg / 1 h / 110 °C

14.1: 33 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; carbon tetrabromide; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dichloro bis(acetonitrile) palladium(II); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; pentane; benzene; 4.1: Stille coupling reaction / 13.1: Curtius rearrangement;
DOI:10.1016/j.tet.2006.07.010