Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Base Information

• Chemical Name: Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester
• CAS No.: 156876-25-4
• Molecular Formula: C₂₈H₂₆N₆O₁₁
• Molecular Weight: 622.548
• Mol file: 156876-25-4.mol

Synonyms:Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Chemical Property of Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

There total 4 articles about Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-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:

N6-(phenoxyacetyl)-2'-deoxyadenosine (110522-74-2) + 5′-(α-methyl-2-nitropiperonyl)oxycarbonyl chloride (156876-26-5) → Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester (156876-25-4)

Guidance literature:

With pyridine; In dichloromethane; at -15 - 20 ℃;

DOI:10.1021/ja964427a

Reference yield:

1-(benzo[d][1,3]dioxol-6-yl)ethanone (3162-29-6) → Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester (156876-25-4)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; sodium tetrahydroborate; nitric acid; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; toluene; 1: Nitration / 2: Reduction / 3: chloroformylation / 4: Esterification;

DOI:10.1021/ja964427a

Reference yield:

methyl 3,4-(methylenedioxy)-6-nitrophenyl ketone (56136-84-6) → Carbonic acid (2R,3S,5R)-3-hydroxy-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester (156876-25-4)

Guidance literature:

Multi-step reaction with 3 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

With pyridine; sodium tetrahydroborate; In tetrahydrofuran; methanol; dichloromethane; toluene; 1: Reduction / 2: chloroformylation / 3: Esterification;

DOI:10.1021/ja964427a

upstream raw materials:

N⁶-(phenoxyacetyl)-2'-deoxyadenosine

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

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

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

Downstream raw materials:

Carbonic acid (2R,3S,5R)-3-[(2-cyano-ethoxy)-diisopropylamino-phosphanyloxy]-5-[6-(2-phenoxy-acetylamino)-purin-9-yl]-tetrahydro-furan-2-ylmethyl ester 1-(6-nitro-benzo[1,3]dioxol-5-yl)-ethyl ester

Refernces