(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

Base Information

• Chemical Name: (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
• CAS No.: 943144-83-0
• Molecular Formula: C₄₄H₇₃NO₉Si
• Molecular Weight: 788.15
• Mol file: 943144-83-0.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 33 articles about (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 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: 76.0%

t-butyldimethylsiyl triflate (69739-34-0) + (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) → (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 (943144-83-0)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

(3E)-3-[(3R)-3,4-isopropylidenedioxybutylidene]-2-tetrahydrofuran (943144-61-4) → (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 (943144-83-0)

Guidance literature:

Multi-step reaction with 24 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

24.1: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °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

Reference yield:

C11H18O4 (943144-62-5) → (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 (943144-83-0)

Guidance literature:

Multi-step reaction with 23 steps

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

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

3.1: Et₃N / CH₂Cl₂ / 1 h / 0 °C

4.1: 91 percent / (DHQD)2PHAL; K₂OsO₂(OH)4; MeSO₂NH₂ / K₃Fe(CN)6; K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 20 °C

5.1: p-TsOH*H₂O / 0.33 h / 20 °C

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

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

7.2: 76 percent / n-Bu₄NI / toluene / 1.5 h / Heating

8.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 20 °C

9.1: K₂CO₃ / methanol / 4 h / 20 °C

10.1: 95 percent / TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 2 h / 20 °C

11.1: 14 percent / LiHMDS / tetrahydrofuran / 1 h / -78 - -20 °C

12.1: 79 percent / aq. DDQ / CH₂Cl₂ / 1 h / 20 °C

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

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

15.1: 64 percent / TBAF; AcOH / tetrahydrofuran / 20 °C

16.1: 2,6-lutidine / CH₂Cl₂ / 11 h / -78 °C

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

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

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

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

21.1: MeOH; concd. HCl / 20 °C

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

23.1: 76 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °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; 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; 4.1: Sharpless asymmetric dihydroxylation / 11.1: Julia coupling reaction / 14.1: Wittig reaction / 22.1: Stille coupling reaction;

DOI:10.1016/j.tetlet.2007.03.152

upstream raw materials:

t-butyldimethylsiyl triflate

(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

(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:

leustroducsin B