1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine
• CAS No.: 1374576-38-1
• Molecular Formula: C₆₁H₈₅N₄O₁₀P
• Molecular Weight: 1065.34
• Mol file: 1374576-38-1.mol

Synonyms:1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

Chemical Property of 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

There total 16 articles about 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine 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: 89.0%

1-[(3'S,5'R,6'R)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(ethoxycarbonyl)methyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine (1374576-29-0) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine (1374576-38-1)

Guidance literature:

With Et₂Nipr₂; In tetrahydrofuran; at 20 ℃;

Reference yield: 89.0%

1-[(3'S,5'R,6'R)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine (1374576-36-9) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine (1374576-38-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo300648u

Reference yield:

(1S,2R,4S,6S)-2-[(tert-butyldimethylsilyl)oxy]-4-[(ethoxycarbonyl)methyl]-6-trimethylsilyloxy-9-oxatricyclo-[4.3.0(1,6).0(2,4)]non-7-ene (1374576-25-6) → 1-[(3'S,5'R,6'S)-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-[(hexadecoxycarbonyl)methyl]-3'-O-[(2-cyanoethoxy)-diisopropylaminophosphanyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine (1374576-38-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BSA / dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 1 h / 20 - 95 °C / Inert atmosphere

3.1: water; potassium hydroxide / ethanol / 2.5 h / 20 °C / Inert atmosphere

4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere; Cooling with ice

5.1: pyridine; hydrogen fluoride / 0 - 45 °C / Inert atmosphere

6.1: pyridine / 23.5 h / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With pyridine; dmap; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; water; tri-n-butyl-tin hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium hydroxide; BSA; In tetrahydrofuran; ethanol; dichloromethane; toluene;

DOI:10.1021/jo300648u

upstream raw materials:

(1S,2R,4S,6S)-2-[(tert-butyldimethylsilyl)oxy]-4-[(ethoxycarbonyl)methyl]-6-trimethylsilyloxy-9-oxatricyclo-[4.3.0(1,6).0(2,4)]non-7-ene

1-[(3'R,5'R,6'S)-3'-O-trimethylsilyl-5'-O-(tert-butyldimethylsilyl)-6'-[(ethoxycarbonyl)methyl]-2'-deoxy-2'-iodo-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

1-[(3'S,5'R,6'S)-3'-O-trimethylsilyl-5'-O-(tert-butyldimethylsilyl)-6'-[(ethoxycarbonyl)methyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

1-[(3'S,5'R,6'R)-5'-O-(tert-butyldimethylsilyl)-6'-(carboxymethyl)-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine