(2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one

Base Information

• Chemical Name: (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one
• CAS No.: 904692-40-6
• Molecular Formula: C₅₂H₈₇NO₈SSi₂
• Molecular Weight: 942.502
• Mol file: 904692-40-6.mol

Synonyms:(2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one

Chemical Property of (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one

There total 29 articles about (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-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: 88.0%

(2S,3R,5R,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-3-hydroxy-5-methoxymethoxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one (904692-22-4) + chloro-trimethyl-silane (75-77-4) → (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one (904692-40-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1021/ol061073b

Reference yield:

7-triisopropylsilanyloxy-hept-1-en-3-ol (904692-26-8) → (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one (904692-40-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 44 percent / 4 Angstroem molecular sieves; (+)-dicyclohexyl tartrate; Ti(O-iPr)4 / t-BuOOH / CH₂Cl₂ / 48 h / -20 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 0 - 20 °C

3.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / -78 - 0 °C

3.2: 81 percent / n-BuLi / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

4.1: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / -78 °C

4.2: 70 percent / dimethylsulfoxide / -78 - -45 °C

5.1: 86 percent / LiBH₄ / methanol; diethyl ether; tetrahydrofuran / 1 h / 0 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

7.1: t-BuOK / tetrahydrofuran / 1 h / 20 °C

7.2: 1.83 g / tetrahydrofuran; toluene

8.1: 95 percent / n-Bu₄BF / tetrahydrofuran / 1 h

9.1: 87 percent / Jones reagent / acetone; H₂O / 0.75 h / 15 °C

10.1: (COCl)2; DMF / CH₂Cl₂ / 1 h

11.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

11.2: 3.93 g / tetrahydrofuran; hexane / 0.75 h / -78 °C

12.1: 81 percent / TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / -78 - 0 °C

13.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With 1-methyl-pyrrolidin-2-one; titanium(IV) isopropylate; dmap; lithium borohydride; n-butyllithium; jones reagent; oxalyl dichloride; (+)-dicyclohexyl tartrate; 4 A molecular sieve; n-Bu₄BF; potassium tert-butylate; sodium hexamethyldisilazane; pivaloyl chloride; titanium tetrachloride; sodium hydride; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; (-)-sparteine; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; 1.1: Sharpless kinetic resolution / 7.2: Wittig methylenation / 9.1: Jones oxidation;

DOI:10.1021/ol061073b

Reference yield:

1 ,5-pentanediol (111-29-5) → (2S,3R,5S,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-5-methoxymethoxy-3-trimethylsilanyloxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one (904692-40-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

1.2: 76 percent / tetrahydrofuran / 0.67 h / 0 °C

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

3.1: Mg / tetrahydrofuran / Heating

3.2: 37.2 g / tetrahydrofuran / 0.08 h / 0 °C

4.1: 44 percent / 4 Angstroem molecular sieves; (+)-dicyclohexyl tartrate; Ti(O-iPr)4 / t-BuOOH / CH₂Cl₂ / 48 h / -20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

5.2: 96 percent / tetrahydrofuran / 0 - 20 °C

6.1: Et₃N; pivaloyl chloride / diethyl ether / 1 h / -78 - 0 °C

6.2: 81 percent / n-BuLi / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

7.1: NaN(SiMe₃)2 / tetrahydrofuran / 1 h / -78 °C

7.2: 70 percent / dimethylsulfoxide / -78 - -45 °C

8.1: 86 percent / LiBH₄ / methanol; diethyl ether; tetrahydrofuran / 1 h / 0 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: t-BuOK / tetrahydrofuran / 1 h / 20 °C

10.2: 1.83 g / tetrahydrofuran; toluene

11.1: 95 percent / n-Bu₄BF / tetrahydrofuran / 1 h

12.1: 87 percent / Jones reagent / acetone; H₂O / 0.75 h / 15 °C

13.1: (COCl)2; DMF / CH₂Cl₂ / 1 h

14.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

14.2: 3.93 g / tetrahydrofuran; hexane / 0.75 h / -78 °C

15.1: 81 percent / TiCl₄; (-)-sparteine; N-methylpyrrolidinone / CH₂Cl₂ / -78 - 0 °C

16.1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 1.5 h / 0 °C

With 1-methyl-pyrrolidin-2-one; titanium(IV) isopropylate; dmap; lithium borohydride; n-butyllithium; jones reagent; oxalyl dichloride; (+)-dicyclohexyl tartrate; 4 A molecular sieve; n-Bu₄BF; potassium tert-butylate; sodium hexamethyldisilazane; pivaloyl chloride; titanium tetrachloride; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; (-)-sparteine; tert.-butylhydroperoxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; acetone; 3.2: Grignard reaction / 4.1: Sharpless kinetic resolution / 10.2: Wittig methylenation / 12.1: Jones oxidation;

DOI:10.1021/ol061073b

upstream raw materials:

(2S,3R,5R,7S)-1-((S)-4-Benzyl-2-thioxo-oxazolidin-3-yl)-7-[(R)-1-(1,1-dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-3-hydroxy-5-methoxymethoxy-2-[(R)-3-((R)-1-vinyl-but-3-enyloxy)-pent-4-enyl]-dec-9-en-1-one

chloro-trimethyl-silane

(R)-2,2-Dimethyl-pent-4-ene-1,3-diol

(R)-3-Hydroxy-2,2-dimethyl-pent-4-enoic acid isobutyl ester