7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine

Base Information

• Chemical Name: 7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine
• CAS No.: 115479-40-8
• Molecular Formula: C₂₀H₃₁ClN₄O₄Si
• Molecular Weight: 455.029
• DSSTox Substance ID: DTXSID501102595
• Mol file: 115479-40-8.mol

Synonyms:115479-40-8;7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine;7H-Pyrrolo[2,3-d]pyrimidin-2-amine, 4-chloro-7-[5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-;4-Chloro-7-[5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine;DTXSID501102595;4-Chloro-7-[5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-beta-D-ribofuranosyl]-7H-;7-((3AR,4R,6R,6aR)-6-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Chemical Property of 7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine

Chemical Property:

• Refractive Index: 1.603
• PSA: 93.65000
• LogP: 4.68740
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 454.1803097
• Heavy Atom Count: 30
• Complexity: 649

Purity/Quality:

97% ^*data from raw suppliers

4-Chloro-7-[5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)N3C=CC4=C3N=C(N=C4Cl)N)CO[Si](C)(C)C(C)(C)C)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](O[C@H]([C@@H]2O1)N3C=CC4=C3N=C(N=C4Cl)N)CO[Si](C)(C)C(C)(C)C)C
• Uses: 4-Chloro-7-[5-O-[(1,1-dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)_x000D_-β-D-ribofuranosyl]-7H-pyrrolo[2,3-d]pyrimidin-2-amine (cas# 115479-40-8) is a compound useful in organic synthesis.

Technology Process of 7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine

There total 8 articles about 7-[(3Ar,4R,6R,6aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-4-chloropyrrolo[2,3-d]pyrimidin-2-amine 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%

2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride (102690-94-8) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) → 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine (115479-40-8)

Guidance literature:

With potassium hydroxide; Tris(3,6-dioxaheptyl)amine; multistep reaction: nucleobase-anion glycosylation of various nucleobases , also with the β-D-ribofuranosyl chloride;

DOI:10.1002/hlca.19900730710

Reference yield: 60.8%

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine (84955-31-7) + 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) → 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine (115479-40-8)

Guidance literature:

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose; With tetrachloromethane; Hexamethylphosphorous triamide; In tetrahydrofuran; at -78 - -20 ℃; for 1.5h;

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine; With sodium hydride; In tetrahydrofuran; acetonitrile; at 20 ℃; for 15.5h;

Reference yield:

2-amino-4-chloro-1H-pyrrolo[2,3-d]pyrimidine + 5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose (217309-46-1) → 4-chloro-7-{5′-O-[(1,1-dimethylethyl)-dimethylsilyl]-2′,3′-O-(1-methylethylidene)-β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine-2-amine (115479-40-8)

Guidance literature:

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; tetrachloromethane; at -76 ℃; for 1h; Nitrogene atmosphere;

2-amino-4-chloro-1H-pyrrolo[2,3-d]pyrimidine; With sodium hydride; In tetrahydrofuran; tetrachloromethane; acetonitrile; for 16h;

upstream raw materials:

2,3-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-α-D-ribofuranosyl chloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

5-O-<(1,1-dimethylethyl)dimethylsilyl>-2,3-O-(1-methylethylidene)-β-D-ribofuranosyl chloride

5-(tert-butyldimethylsilyloxy)-2,3-isopropylidenedioxy-D-ribofuranose

Downstream raw materials:

7-deazaguanosine

2-amino-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidin-4(3H)-one

2-Amino-4-methoxy-7-β-D-ribofuranosylpyrrolo<2,3-d>pyrimidine

2-[(4-monomethoxytrityl)amino]-7-(2-O-methyl-β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one

Refernces

• 1、 Malnuit, Vincent,Slavětínská, Lenka Po?tová,Nau?, Petr,D?ubák, Petr,Hajdúch, Marián,Stola?íková, Ji?ina,Sná?el, Jan,Pichová, Iva,Hocek, Michal. "2-substituted 6-(het)aryl-7-deazapurine ribonucleosides: Synthesis, inhibition of adenosine kinases, and antimycobacterial activity". . p. 1079 - 1093. Retrieved 2015.
• 2、 Hulpia, Fabian,Bouton, Jakob,Campagnaro, Gustavo D.,Alfayez, Ibrahim A.,Mabille, Dorien,Maes, Louis,de Koning, Harry P.,Caljon, Guy,Van Calenbergh, Serge. "C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents". . . Retrieved 2020/01/13.