ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Base Information

• Chemical Name: ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate
• CAS No.: 191935-25-8
• Molecular Formula: C₃₁H₄₈O₁₂S
• Molecular Weight: 644.781
• Mol file: 191935-25-8.mol

Synonyms:ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Chemical Property of ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

There total 18 articles about ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate 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: 51.0%

[(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolan-4-yl]-oxo-acetic acid ethyl ester (191935-10-1) + (R,Z)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane (191934-88-0) → ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (871514-57-7) + ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191935-25-8)

Guidance literature:

With tin(II) trifluoromethanesulfonate; In various solvent(s); at -70 ℃; for 1.5h;

DOI:10.1016/j.tet.2005.09.030

Reference yield: 23.0%

ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (871514-57-7) → ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191935-25-8) + S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 - -23 ℃;

DOI:10.1016/j.tet.2005.09.030

Reference yield: 23.0%

[(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolan-4-yl]-oxo-acetic acid ethyl ester (191935-10-1) + S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate (871514-33-9) → ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (871514-57-7) + ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191935-25-8)

Guidance literature:

S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.5h;

[(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolan-4-yl]-oxo-acetic acid ethyl ester; In tetrahydrofuran; toluene; at -78 - -23 ℃;

DOI:10.1016/j.tet.2005.09.030

upstream raw materials:

ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate

[(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolan-4-yl]-oxo-acetic acid ethyl ester

S-methyl (2S,3R)-4-benzyloxy-2,3-(dimethylmethylenedioxy)butanethioate

(R,Z)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane

Downstream raw materials:

ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[1,2-(diethylmethylenedioxy)-3-[(2-methoxyethoxy)methoxy]propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methoxycarbonyl)pentanoate

3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)-7-dodecyne-1,2,3-tricarboxylate

3-ethyl 1,2-dimethyl (1S,2S,3R,4R,5R,10R,11R)-10-benzyloxy-4,5-(diethylmethylenedioxy)-1,2-(dimethylmethylenedioxy)-11-methyl-6-oxo-12-phenyl-3-(trimethylsilyloxy)dodecane-1,2,3-tricarboxylate

5-ethyl 3,4-dimethyl [1S,1(4R,5R),3S,4S,5R,6R,7R]-1-(4-benzyloxy-5-methyl-6-phenylhexyl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylate