Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

Base Information

Chemical Name:Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester
CAS No.:473759-08-9
Molecular Formula:C₃₇H₆₁NO₇Si
Molecular Weight:659.979
Hs Code.:

Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

Synonyms:Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

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Chemical Property of Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

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Technology Process of Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

There total 11 articles about Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl 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: 52.0%

: 473759-05-6
Isobutyric acid (1S,2S,3R,4R)-1-(2-benzyloxy-ethyl)-3-hydroxy-2,4-dimethyl-5-oxo-pentyl ester

: 473758-95-1
[(Z)-(3R,4R,5R)-7-(Formyl-methyl-amino)-3,5-dimethyl-2-oxo-4-triethylsilanyloxy-hept-6-enyl]-phosphonic acid dimethyl ester

: 473759-08-9
Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; acetonitrile; at 20 ℃; for 3h;
DOI:10.1016/S0040-4039(02)01217-0

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 473759-08-9
Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

2: 90 percent / LiBH₄ / tetrahydrofuran / 24 h / -78 - 20 °C

3: 87 percent / NaIO₄ / methanol; H₂O / 2 h / 0 - 20 °C / pH 7

4: tetrahydrofuran / 2 h / -78 °C

5: 73 percent / DDQ / CH₂Cl₂; H₂O / 0.5 h / 20 °C / pH 7

6: 80 percent / TPAP; NMO / CH₂Cl₂ / 0.5 h / 20 °C

7: 72 percent / n-BuLi / tetrahydrofuran / 4 h / -78 °C

8: 81 percent / TPAP; NMO / CH₂Cl₂ / 1 h / 20 °C

9: 52 percent / LiCl; DBU / tetrahydrofuran; acetonitrile / 3 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; lithium borohydride; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 4: Wittig olefination / 9: Horner-Wadsworth-Emmons coupling;
DOI:10.1016/S0040-4039(02)01217-0

Reference yield:

: 473759-03-4
N-((Z)-(3R,4R,5R)-3,5-Dimethyl-6-oxo-4-triethylsilanyloxy-hex-1-enyl)-N-methyl-formamide

: 473759-08-9
Isobutyric acid (5E,11Z)-(1S,2S,3S,4S,8R,9R,10R)-1-(2-benzyloxy-ethyl)-12-(formyl-methyl-amino)-3-hydroxy-2,4,8,10-tetramethyl-7-oxo-9-triethylsilanyloxy-dodeca-5,11-dienyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 72 percent / n-BuLi / tetrahydrofuran / 4 h / -78 °C

2: 81 percent / TPAP; NMO / CH₂Cl₂ / 1 h / 20 °C

3: 52 percent / LiCl; DBU / tetrahydrofuran; acetonitrile / 3 h / 20 °C

With n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; dichloromethane; acetonitrile; 3: Horner-Wadsworth-Emmons coupling;
DOI:10.1016/S0040-4039(02)01217-0