(R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester

Base Information

• Chemical Name: (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester
• CAS No.: 194654-02-9
• Molecular Formula: C₃₀H₄₃N₃O₇
• Molecular Weight: 557.687
• Mol file: 194654-02-9.mol

Synonyms:(R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester

Chemical Property of (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester

There total 12 articles about (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester 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: 75.0%

(R)-4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-ethyl-butyric acid benzyl ester (194653-91-3) + (2R,3R)-2-((R)-4-Azido-1-ethyl-butyl)-3-((Z)-propenyl)-oxirane → (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester (194654-02-9)

Guidance literature:

tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ethriol phosphite; In tetrahydrofuran; for 12h; Ambient temperature;

DOI:10.1002/anie.199714861

Reference yield:

cycl-isopropylidene malonate (2033-24-1) → (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester (194654-02-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaTeH, piperidine, HOAc / ethanol

2: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

With piperidine; sodium hydrogen telluride; acetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ethriol phosphite; In tetrahydrofuran; ethanol;

DOI:10.1002/anie.199714861

Reference yield:

(R)-5-azido-2-ethylpentanal (194653-99-1) → (R)-4-[5-((E)-(1R,4S,5R)-8-Azido-5-ethyl-4-hydroxy-1-methyl-oct-2-enyl)-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl]-2-ethyl-butyric acid benzyl ester (194654-02-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 85 percent / NaH / tetrahydrofuran / Ambient temperature

2: 95 percent / DIBAL-H / tetrahydrofuran / -78 °C

3: 70 percent / Ti(O-i-C₃H₇)4, (-)-DET, MS 4A / CH₂Cl₂ / 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 2.) -78 deg C

5: KN(SiMe₃)2 / tetrahydrofuran

6: 75 percent / <(dba)3Pd₂*CHCl₃>, 4-ethyl-2,6,7-trioxa-1-phosphabicyclo<2.2.2>octane / tetrahydrofuran / 12 h / Ambient temperature

With titanium(IV) isopropylate; oxalyl dichloride; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ethriol phosphite; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.199714861

upstream raw materials:

(R)-4-(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-ethyl-butyric acid benzyl ester

cycl-isopropylidene malonate

(R)-5-azido-2-ethyl-1-pentanol

(R)-5-azido-2-ethylpentanal

Downstream raw materials:

(3R,6R,7R,10R,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-3,11-diethyl-7-methyl-2-oxo-azacyclotetradecane-6-carboselenoic acid Se-phenyl ester

(R)-4-{5-[(E)-(1R,4S,5R)-8-Azido-4-(tert-butyl-dimethyl-silanyloxy)-5-ethyl-1-methyl-oct-2-enyl]-2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl}-2-ethyl-butyric acid benzyl ester