(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

Base Information

Chemical Name:(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
CAS No.:194654-11-0
Molecular Formula:C₃₆H₅₇N₃O₇Si
Molecular Weight:671.95
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 14 articles about (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 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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 194654-02-9
(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

: 194654-11-0
(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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃;
DOI:10.1002/anie.199714861

Reference yield:

: 2033-24-1
cycl-isopropylidene malonate

: 194654-11-0
(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

Guidance literature:: Multi-step reaction with 3 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

3: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With piperidine; 2,6-dimethylpyridine; sodium hydrogen telluride; acetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; ethriol phosphite; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1002/anie.199714861

Reference yield:

: 194653-98-0
(R)-5-azido-2-ethyl-1-pentanol

: 194654-11-0
(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

Guidance literature:: Multi-step reaction with 8 steps

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

2: 85 percent / NaH / tetrahydrofuran / Ambient temperature

3: 95 percent / DIBAL-H / tetrahydrofuran / -78 °C

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

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

6: KN(SiMe₃)2 / tetrahydrofuran

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

8: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

With 2,6-dimethylpyridine; 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