(S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester

Base Information

• Chemical Name: (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester
• CAS No.: 467234-66-8
• Molecular Formula: C₃₈H₅₉NO₉
• Molecular Weight: 673.888
• Mol file: 467234-66-8.mol

Synonyms:(S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester

Chemical Property of (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester

There total 40 articles about (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester 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: 85.0%

(S)-6-Methyl-octanoic acid (1S,3R)-3-((1Z,3Z)-4-{(4R,6R)-6-[(E)-(R)-1-(2-allyloxycarbonylamino-ethyl)-3-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-allyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-buta-1,3-dienyl)-cyclohexyl ester (467234-65-7) → (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-66-8)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(02)00528-8

Reference yield:

(1S,3R)-3-[2-(Z)-tributylstannylvinyl]cyclohexyl (S)-6-methyloctanoate + C21H30INO7 (943144-82-9) → (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-66-8)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; at 20 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

(3E)-3-[(3R)-3,4-isopropylidenedioxybutylidene]-2-tetrahydrofuran (943144-61-4) → (S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester (467234-66-8)

Guidance literature:

Multi-step reaction with 23 steps

1.1: DIBAlH / toluene / 0.33 h / -78 °C

2.1: imidazole / dimethylformamide / 0.5 h / 20 °C

3.1: NaBH₄; CeCl₃*7H₂O / methanol / 0.25 h / -78 °C

4.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

5.1: 91 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; MeSO₂NH₂ / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

6.1: p-TsOH*H₂O / 0.33 h / 20 °C

7.1: Zn(NO₃)2*6H₂O / acetonitrile / 3 h / 50 °C

8.1: n-Bu₂SnO / toluene / 12 h / Heating

8.2: 76 percent / n-Bu₄NI / toluene / 1.5 h / Heating

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

10.1: K₂CO₃ / methanol / 4 h / 20 °C

11.1: 95 percent / TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

12.1: 14 percent / LiHMDS / tetrahydrofuran / 1 h / -78 - -20 °C

13.1: 79 percent / aq. DDQ / CH₂Cl₂ / 1 h / 20 °C

14.1: TEMPO; DAIB / CH₂Cl₂ / 1.5 h / 20 °C

15.1: NaHMDS; HMPA / tetrahydrofuran / 0.5 h / -100 - 0 °C

16.1: 64 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

17.1: 2,6-lutidine / CH₂Cl₂ / 11 h / -78 °C

18.1: p-TsOH*H₂O / tetrahydrofuran; methanol / 1 h / 0 °C

19.1: Ph₃P; DPPA; DEAD / tetrahydrofuran / 1 h / 20 °C

20.1: Ph₃P; H₂O / tetrahydrofuran / 20 h / 20 °C

21.1: pyridine / tetrahydrofuran / 0.33 h / 20 °C

22.1: MeOH; concd. HCl / 20 °C

23.1: PdCl₂(MeCN)2 / dimethylformamide / 1.5 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloro bis(acetonitrile) palladium(II); 2,2,6,6-tetramethyl-piperidine-N-oxyl; zinc(II) nitrate; sodium tetrahydroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; potassium dioxotetrahydroxoosmate(VI); methanesulfonamide; [bis(acetoxy)iodo]benzene; MS 4 Angstroem; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; diethylazodicarboxylate; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 5.1: Sharpless asymmetric dihydroxylation / 12.1: Julia coupling reaction / 15.1: Wittig reaction / 23.1: Stille coupling reaction;

DOI:10.1016/j.tetlet.2007.03.152

upstream raw materials:

(S)-6-Methyl-octanoic acid (1S,3R)-3-((1Z,3Z)-4-{(4R,6R)-6-[(E)-(R)-1-(2-allyloxycarbonylamino-ethyl)-3-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-allyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-buta-1,3-dienyl)-cyclohexyl ester

C₂₁H₃₀INO₇

(2R,3S)-3-ethyl-6-(4-methoxybenzyloxy)-4-hexyne-1,2-diol

(2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

Downstream raw materials:

(5S,6S)-6-[(1E,3R,4R,6R,7Z,9Z)-3-[2-(allyloxycarbonylamino)ethyl]-6-tert-butyldimethylsiloxy-3,4-dihydroxy-10-[(1R,3S)-3-[(6S)-methyloctanoyloxy]cyclohexyl]-1,7,9-decatrienyl]-5-ethyl-5,6-dihydro-2H-pyran-2-one

leustroducsin B

(6S)-6-methyloctanoic acid

(S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7-dihydroxy-8-trimethylsilanyloxy-deca-1,3,9-trienyl]-cyclohexyl ester