Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester

Base Information

• Chemical Name: Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester
• CAS No.: 272775-99-2
• Molecular Formula: C₄₁H₅₀N₈O₇Si
• Molecular Weight: 794.983

Synonyms:Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester

Chemical Property of Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester

There total 29 articles about Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-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: 65.0%

6-chloro- 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine (222296-31-3) + Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester (272775-98-1) → Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester (272775-99-2)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 130 ℃; for 2.5h;

DOI:10.1021/ol005715l

Reference yield:

(+/-)-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol (35949-66-7,58526-04-8,104873-72-5,115509-74-5) → Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester (272775-99-2)

Guidance literature:

Multi-step reaction with 25 steps

1: NaH; Bu₄NI / tetrahydrofuran; dimethylformamide / 20 °C

2: aq. AcOH / 50 °C

3: 41 percent / DCC; DMAP / CH₂Cl₂ / -20 °C

4: 85 percent / NaOMe / methanol / 50 °C

5: pyridine / 20 °C

6: pyridine / 20 °C

7: NaN₃ / dimethylformamide / 100 °C

8: NaOMe / methanol / 20 °C

9: pyridine / 20 °C

10: 18-crown-6 / dimethylformamide / 100 °C

11: DDQ; H₂O / CH₂Cl₂ / 0 °C

12: NaOMe / methanol / 20 °C

13: NaIO₄ / H₂O; methanol / 20 °C

14: NaBH₄ / methanol / 0 °C

15: p-TsOH / dimethylformamide / 20 °C

16: DMSO; DCC; TFA / pyridine; benzene / 20 °C

17: diethyl ether / -115 °C

18: NaH / dimethylformamide / 0 °C

19: O₃ / CH₂Cl₂ / -78 °C

20: p-TsOH / methanol / 0 °C

21: pyridine / 20 °C

22: trimethylsilyl bromide / CHCl₃ / 20 °C

23: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 20 °C

24: 78 percent / H₂ / Lindlar catalyst / toluene / 20 °C / 760.05 Torr

25: NaOt-Bu; Pd₂(dba)3; (R)-(+)-BINAP / toluene / 1 h / 130 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 18-crown-6 ether; trimethylsilyl bromide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1: Etherification / 2: Hydrolysis / 3: Acylation / 4: deacylation / 5: Acylation / 6: mesylation / 7: Substitution / 8: deacylation / 9: mesylation / 10: Acetoxylation / 11: Substitution / 12: Deacetylation / 13: Oxidation / 14: Reduction / 15: Condensation / 16: Moffatt oxidation / 17: Addition / 18: Etherification / 19: ozonolysis / 20: Hydrolysis / 21: Acetylation / 22: Substitution / 23: Substitution / 24: Hydrogenation / 25: Substitution;

DOI:10.1021/ol005715l

Reference yield:

DL-1,4-Di-O-benzyl-5,6-bis-O-(4-methoxybenzyl)-myo-inositol (111331-59-0,111465-38-4,113084-85-8) → Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester (272775-99-2)

Guidance literature:

Multi-step reaction with 23 steps

1: 41 percent / DCC; DMAP / CH₂Cl₂ / -20 °C

2: 85 percent / NaOMe / methanol / 50 °C

3: pyridine / 20 °C

4: pyridine / 20 °C

5: NaN₃ / dimethylformamide / 100 °C

6: NaOMe / methanol / 20 °C

7: pyridine / 20 °C

8: 18-crown-6 / dimethylformamide / 100 °C

9: DDQ; H₂O / CH₂Cl₂ / 0 °C

10: NaOMe / methanol / 20 °C

11: NaIO₄ / H₂O; methanol / 20 °C

12: NaBH₄ / methanol / 0 °C

13: p-TsOH / dimethylformamide / 20 °C

14: DMSO; DCC; TFA / pyridine; benzene / 20 °C

15: diethyl ether / -115 °C

16: NaH / dimethylformamide / 0 °C

17: O₃ / CH₂Cl₂ / -78 °C

18: p-TsOH / methanol / 0 °C

19: pyridine / 20 °C

20: trimethylsilyl bromide / CHCl₃ / 20 °C

21: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 20 °C

22: 78 percent / H₂ / Lindlar catalyst / toluene / 20 °C / 760.05 Torr

23: NaOt-Bu; Pd₂(dba)3; (R)-(+)-BINAP / toluene / 1 h / 130 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; sodium azide; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 18-crown-6 ether; trimethylsilyl bromide; trimethylsilylazide; tetrabutyl ammonium fluoride; water; hydrogen; sodium methylate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; dicyclohexyl-carbodiimide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium t-butanolate; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; benzene; 1: Acylation / 2: deacylation / 3: Acylation / 4: mesylation / 5: Substitution / 6: deacylation / 7: mesylation / 8: Acetoxylation / 9: Substitution / 10: Deacetylation / 11: Oxidation / 12: Reduction / 13: Condensation / 14: Moffatt oxidation / 15: Addition / 16: Etherification / 17: ozonolysis / 18: Hydrolysis / 19: Acetylation / 20: Substitution / 21: Substitution / 22: Hydrogenation / 23: Substitution;

DOI:10.1021/ol005715l

upstream raw materials:

6-chloro- 9-((2-(trimethylsilyl)ethoxy)methyl)-9H-purine

Acetic acid (S)-2-((2R,3R,4R,5R,6S)-6-amino-3-azido-4,5-bis-benzyloxy-tetrahydro-pyran-2-yl)-2-benzyloxy-ethyl ester

D-myo-inositol

(+/-)-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 272775-99-2 Acetic acid (S)-2-{(2R,3R,4R,5R,6S)-3-azido-4,5-bis-benzyloxy-6-[9-(2-trimethylsilanyl-ethoxymethyl)-9H-purin-6-ylamino]-tetrahydro-pyran-2-yl}-2-benzyloxy-ethyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send