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

Base Information

• Chemical Name: ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate
• CAS No.: 191934-95-9
• Molecular Formula: C₃₂H₄₂O₁₀S
• Molecular Weight: 618.745
• Mol file: 191934-95-9.mol

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

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

There total 13 articles about ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)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: 62.0%

ethyl (3R,4S)-5-benzyloxy-4,5-(dimethylmethylenedioxy)-2-oxopentanoate (191934-92-6) + (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-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191934-95-9) + ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191934-93-7)

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:

ethyl (3R,4S)-5-benzyloxy-4,5-(dimethylmethylenedioxy)-2-oxopentanoate (191934-92-6) + (R,E)-4-(benzyloxy)methyl-5-[methylthio(trimethylsilyloxy)methylene]-2,2-dimethyl-1,3-dioxolane (191934-90-4) → ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191934-95-9) + ethyl [2R,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191934-93-7)

Guidance literature:

With tin(II) trifluoromethanesulfonate; propiononitrile; at -55 ℃; for 1h; Yield given. Yields of byproduct given;

DOI:10.1055/s-1997-6154

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-D-threose (81801-09-4) → ethyl [2S,2(1R,2S),3S,4R]-5-benzyloxy-2-[3-benzyloxy-1,2-(dimethylmethylenedioxy)propyl]-3,4-(dimethylmethylenedioxy)-2-hydroxy-3-(methylthio)carbonylpentanoate (191934-95-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / 2-methyl-2-butene; NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

2.1: oxalyl chloride; DMF / CH₂Cl₂ / 1.5 h / 20 °C

3.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

4.1: KHMDS / toluene; tetrahydrofuran / 0.5 h / -78 °C

4.2: 87 percent / toluene; tetrahydrofuran / -78 - 20 °C

5.1: Sn(OTf)2 / various solvent(s) / 1 h / -55 °C

With sodium chlorite; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; 2-methyl-but-2-ene; oxalyl dichloride; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol; 5.1: aldol coupling;

DOI:10.1016/j.tet.2005.09.030

upstream raw materials:

ethyl (3R,4S)-5-benzyloxy-4,5-(dimethylmethylenedioxy)-2-oxopentanoate

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

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

(2R,3S)-4-benzyloxy-2,3-(dimethylmethylenedioxy)-N-methoxy-N-methylbutanamide

Downstream raw materials:

(1S,4S,8R)-8-Benzyloxymethyl-1-((4R,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-6,6-dimethyl-3-oxo-2,5,7-trioxa-spiro[3.4]octane-1-carboxylic acid ethyl ester