(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Base Information

Chemical Name:(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one
CAS No.:942618-53-3
Molecular Formula:C₄₅H₆₁NO₅Si
Molecular Weight:724.069
Hs Code.:

(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Synonyms:(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Suppliers and Price of (2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

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Chemical Property of (2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

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Technology Process of (2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

There total 16 articles about (2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-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: 49.0%

: 942618-52-2
(1R,2S,2'S,2''E,3S,4R,4''E,6S,6''E,8''R,10''S,12''E,14''R)-4-acetoxy-2,3-epoxy-6-hydroxy-1-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexan-1-ol

: 942618-53-3
(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;
DOI:10.1021/jo070337k

Reference yield:

: 942618-33-9
(3S,5S,8R,10S)-3-benzyloxycarbonylamino-8-hydroxy-10-triethylsilyloxy-1-oxaspiro[4,5]dec-6-en-2-one

: 942618-53-3
(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 9 steps

1: 99 percent / mCPBA / CH₂Cl₂ / 24 h / 20 °C

2: 99 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 - 20 °C

3: 94 percent / NaBH₄ / ethanol / 9 h / 0 °C

4: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

5: 83 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

6: 84 percent / mCPBA / CH₂Cl₂ / 70 h / 0 °C

7: H₂; AcOH / Pd(OH)2/C / methanol / 0.5 h / 20 °C / 760.05 Torr

8: 40.2 mg / EDCI; diisopropylethylamine / dimethylformamide / 12 h / 0 - 20 °C

9: 49 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; 9: Swern oxidation;
DOI:10.1021/jo070337k

Reference yield:

: 942618-32-8
(3S,5S,10S)-3-benzyloxycarbonylamino-10-triethylsilyloxy-1-oxaspiro[4,5]dec-6-ene-2,8-dione

: 942618-53-3
(2'S,2''E,4S,4''E,5S,6S,6''E,8''R,10''S,12''E,14''R)-4,5-epoxy-6-hydroxy-6-[2'-(8'',10'',12'',14''-tetramethylhexadeca-2'',4'',6'',12''-tetraenoylamino)-3'-tert-butyldiphenylsilyloxy-propyl]-2-cyclohexen-1-one

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / NaBH₄; CeCl₃*7H₂O / propan-2-ol; tetrahydrofuran / 0.67 h / 0 °C

2: 99 percent / mCPBA / CH₂Cl₂ / 24 h / 20 °C

3: 99 percent / pyridine; DMAP / CH₂Cl₂ / 24 h / 0 - 20 °C

4: 94 percent / NaBH₄ / ethanol / 9 h / 0 °C

5: 94 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

6: 83 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

7: 84 percent / mCPBA / CH₂Cl₂ / 70 h / 0 °C

8: H₂; AcOH / Pd(OH)2/C / methanol / 0.5 h / 20 °C / 760.05 Torr

9: 40.2 mg / EDCI; diisopropylethylamine / dimethylformamide / 12 h / 0 - 20 °C

10: 49 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 10: Swern oxidation;
DOI:10.1021/jo070337k