(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

Base Information

Chemical Name:(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal
CAS No.:618096-15-4
Molecular Formula:C₃₈H₅₈O₆Si
Molecular Weight:638.96
Hs Code.:

Synonyms:(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

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Chemical Property of (2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

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Technology Process of (2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

There total 12 articles about (2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal 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: 97.0%

: 618095-96-8
(2S,3S,4S,5S,6S,9RS,10S,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-1,9-tridecanediol

: 618096-15-4
(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -45 - 20 ℃;
DOI:10.1021/ol035227o

Reference yield:

: 108393-30-2
(2R,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol

: 618096-15-4
(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

Guidance literature:: Multi-step reaction with 7 steps

1.1: DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

1.2: NaH; TBAI / tetrahydrofuran / 16 h / 60 °C

1.3: 6.5 g / AlCl₃ / m-xylene; CH₂Cl₂ / 1 h / -40 - -20 °C

2.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -30 - -10 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: 42 percent / H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

5.1: H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

6.1: 90 percent / lithium di-t-butylbiphenylide; Li / tetrahydrofuran / 4 h / -45 °C

7.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -45 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; lithium di-t-butylbiphenylide; hydrogen; lithium; dimethyl sulfoxide; triethylamine; Pt/Al₂O₃; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1021/ol035227o

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 618096-15-4
(2R,3R,4S,5S,6S,10R,11R,12R)-13-tert-butyldiphenylsilyloxy-3,5-isopropylidenedioxy-11-methoxy-2,4,6,10,12-pentamethyl-9-oxotridecanal

Guidance literature:: Multi-step reaction with 7 steps

1.1: DMAP; imidazole / CH₂Cl₂ / 0.5 h / 20 °C

1.2: NaH; TBAI / tetrahydrofuran / 16 h / 60 °C

1.3: 6.5 g / AlCl₃ / m-xylene; CH₂Cl₂ / 1 h / -40 - -20 °C

2.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -30 - -10 °C

3.2: 87 percent / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.1: 42 percent / H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

5.1: H₂ / Pt/alumina / ethyl acetate / 192 h / 20 °C / 11400 Torr

6.1: 90 percent / lithium di-t-butylbiphenylide; Li / tetrahydrofuran / 4 h / -45 °C

7.1: 97 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -45 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; lithium di-t-butylbiphenylide; hydrogen; lithium; dimethyl sulfoxide; triethylamine; Pt/Al₂O₃; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 2.1: Swern oxidation / 7.1: Swern oxidation;
DOI:10.1021/ol035227o