acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Base Information

Chemical Name:acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester
CAS No.:719278-97-4
Molecular Formula:C₃₈H₅₉N₅O₁₀SSi₂
Molecular Weight:834.151
Hs Code.:

acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-<i>c</i>]pyran-4-yl)-1-[3,4-bis-(<i>tert</i>-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2<i>H</i>-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Chemical Property of acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

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Technology Process of acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

There total 18 articles about acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl 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:

: 719278-96-3
1-[(2R,3R,4R,5R)-5-[(R)-2-((3aS,4R,6S,7R,7aR)-7-Azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-hydroxy-ethyl]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione

: 108-24-7
acetic anhydride

: 719278-97-4
acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: With dmap; triethylamine; In acetonitrile; at 20 ℃; for 12h;
DOI:10.1081/NCN-120027831

Reference yield:

: (3aR,4S,6R,7R,7aR)-7-Azido-2,2-dimethyl-4-phenylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

: 719278-97-4
acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: 1.83 g / sodium borohydride / methanol / 0.5 h / -20 °C

2.1: imidazole / dimethylformamide / 1 h / 0 °C

3.1: pyridine / 12 h / 20 °C

4.1: 534 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

5.1: pyridine / CH₂Cl₂ / 0.08 h / -20 °C

6.1: 614 mg / Et₃N / CH₂Cl₂ / 1 h / 20 °C

7.1: 90 percent / NaOMe / methanol / 1 h / 20 °C

8.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

9.1: samarium diiodide; O₂ / tetrahydrofuran / -40 °C

9.2: tetrahydrofuran / 0 °C

10.1: 55 mg / sodium borohydride; AcOH / CH₂Cl₂ / 0.5 h / -20 °C

11.1: 32 mg / mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

12.1: Tf₂O; pyridine / CH₂Cl₂ / 0.08 h / -20 °C

13.1: 21 mg / Et₃N; DMAP / acetonitrile / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; samarium diiodide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; oxygen; sodium methylate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/NCN-120027831

Reference yield:

: 719278-88-3
(2S,3R,4S,5R)-2-azido-3,4-(dimethylmethylenedioxy)-6-phenylthio-1,5-hexanediol

: 719278-97-4
acetic acid 2-(7-azido-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl)-1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole / dimethylformamide / 1 h / 0 °C

2.1: pyridine / 12 h / 20 °C

3.1: 534 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

4.1: pyridine / CH₂Cl₂ / 0.08 h / -20 °C

5.1: 614 mg / Et₃N / CH₂Cl₂ / 1 h / 20 °C

6.1: 90 percent / NaOMe / methanol / 1 h / 20 °C

7.1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: samarium diiodide; O₂ / tetrahydrofuran / -40 °C

8.2: tetrahydrofuran / 0 °C

9.1: 55 mg / sodium borohydride; AcOH / CH₂Cl₂ / 0.5 h / -20 °C

10.1: 32 mg / mCPBA / CH₂Cl₂ / 0.5 h / 0 °C

11.1: Tf₂O; pyridine / CH₂Cl₂ / 0.08 h / -20 °C

12.1: 21 mg / Et₃N; DMAP / acetonitrile / 12 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; samarium diiodide; trifluoromethylsulfonic anhydride; tetrabutyl ammonium fluoride; oxygen; sodium methylate; Dess-Martin periodane; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/NCN-120027831