5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate

Base Information

• Chemical Name: 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate
• CAS No.: 190850-08-9
• Molecular Formula: C₃₂H₃₂N₇O₁₅P
• Molecular Weight: 785.618

Synonyms:5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate

Chemical Property of 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate

Chemical Property:

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Technology Process of 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate

There total 7 articles about 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N²-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate 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: 77.0%

5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N2-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphite → 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N2-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate (190850-08-9)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; water; for 0.0833333h;

DOI:10.1021/ja964427a

Reference yield:

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N2-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate (190850-08-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 66 percent / HNO₃ / acetic acid; H₂O / 3.75 h / 3 - 20 °C

2: 98 percent / sodium borohydride / methanol / 3.5 h / 5 - 20 °C

3: 205 g / toluene; tetrahydrofuran / 42 h / 20 °C

4: pyridine / CH₂Cl₂ / -15 - 20 °C

5: diisopropylammonium tetrazolide / CH₂Cl₂

6: 57 percent / tetrazole / acetonitrile / 0.25 h

7: 77 percent / H₂O₂ / H₂O; tetrahydrofuran / 0.08 h

With pyridine; 1H-tetrazole; sodium tetrahydroborate; N,N-diisopropylamine tetrazolide; dihydrogen peroxide; nitric acid; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; toluene; acetonitrile; 1: Nitration / 2: Reduction / 3: chloroformylation / 4: Esterification / 5: phosphitylation / 6: methanolysis / 7: Oxidation;

DOI:10.1021/ja964427a

Reference yield:

methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone (56136-84-6) → 5'-O-[(R,S)-(1-(3,4-(methylenedioxy)-6-nitrophenyl)ethoxy)carbonyl]-N2-(phenoxyacetyl)-2'-deoxyguanosine 3'-O-(2-cyanoethyl)methyl phosphate (190850-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / sodium borohydride / methanol / 3.5 h / 5 - 20 °C

2: 205 g / toluene; tetrahydrofuran / 42 h / 20 °C

3: pyridine / CH₂Cl₂ / -15 - 20 °C

4: diisopropylammonium tetrazolide / CH₂Cl₂

5: 57 percent / tetrazole / acetonitrile / 0.25 h

6: 77 percent / H₂O₂ / H₂O; tetrahydrofuran / 0.08 h

With pyridine; 1H-tetrazole; sodium tetrahydroborate; N,N-diisopropylamine tetrazolide; dihydrogen peroxide; In tetrahydrofuran; methanol; dichloromethane; water; toluene; acetonitrile; 1: Reduction / 2: chloroformylation / 3: Esterification / 4: phosphitylation / 5: methanolysis / 6: Oxidation;

DOI:10.1021/ja964427a

upstream raw materials:

1-(benzo[d][1,3]dioxol-6-yl)ethanone

methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone

(R,S)-1-[4',5'-(methylenedioxy)-2'-nitrophenyl]ethanol

5′-(α-methyl-2-nitropiperonyl)oxycarbonyl chloride

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