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

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-(methoxycarbonyl)pentanoate
• CAS No.: 191935-26-9
• Molecular Formula: C₃₁H₄₈O₁₃
• Molecular Weight: 628.714
• Mol file: 191935-26-9.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-(methoxycarbonyl)pentanoate

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-(methoxycarbonyl)pentanoate

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-(methoxycarbonyl)pentanoate

There total 16 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-(methoxycarbonyl)pentanoate 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: 87.0%

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) → 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 (191935-26-9)

Guidance literature:

With mercury(II) trifluoroacetate; In methanol; for 10h; Heating;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolane-4-carbaldehyde (871514-68-0) → 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 (191935-26-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 79 percent / NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / H₂O; 2-methyl-propan-2-ol / 8 h / 20 °C

2.1: 89 percent / diethyl cyanophosphonate; Et₃N / dimethylformamide / 1.5 h / 20 °C

3.1: tert-butyllithium / pentane; tetrahydrofuran / 0.5 h / -78 - 0 °C

3.2: 90 percent / tetrahydrofuran; pentane / 0.5 h / -78 °C

4.1: ozone / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 86 percent / Me₂S / CH₂Cl₂ / 1 h / -78 - 20 °C

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

5.2: 12 percent / tetrahydrofuran; toluene / -78 - -23 °C

6.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

7.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl cyanophosphonate; tert.-butyl lithium; mercury(II) trifluoroacetate; potassium hexamethylsilazane; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; pentane; 6.1: aldol coupling;

DOI:10.1016/j.tet.2005.09.030

Reference yield:

(4S,5R)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolane-4-carbonyl chloride → 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 (191935-26-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 77 percent / n-Bu₄NI / CH₂Cl₂; H₂O / 0.17 h / 0 °C

2.1: butyllithium; 1,1,1,3,3,3-hexamethyldisilazane / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 95 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 32 percent / Sn(OTf)2 / various solvent(s) / 1.5 h / -70 °C

4.1: 23 percent / KHMDS / toluene; tetrahydrofuran / -78 - -23 °C

5.1: 87 percent / Hg(OCOCF₃)2 / methanol / 10 h / Heating

With tin(II) trifluoromethanesulfonate; n-butyllithium; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 4.1: aldol coupling;

DOI:10.1016/j.tet.2005.09.030

upstream 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-(methylthio)carbonylpentanoate

(4R,5S)-2,2-Diethyl-5-(2-methoxy-ethoxymethoxymethyl)-[1,3]dioxolane-4-carbaldehyde

(2S,3S)-2,3-diethylmethylenedioxy-4-[(2-methoxyethoxy)methoxy]-1-butanol

(2R,3S)-2,3-diethylmethylenedioxy-4-[(2-methoxyethoxy)methoxy]butyric acid

Downstream raw materials:

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

(4S,5S)-4-{(R)-[(4R,5S)-5-((5R,6R)-5-Benzyloxy-1-hydroxy-6-methyl-7-phenyl-hept-2-ynyl)-2,2-diethyl-[1,3]dioxolan-4-yl]-ethoxycarbonyl-trimethylsilanyloxy-methyl}-2,2-dimethyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester