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

Base Information

Chemical Name: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
CAS No.:1374576-36-9
Molecular Formula:C₅₂H₆₈N₂O₉
Molecular Weight:865.12
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 11 articles about 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 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: 69.0%

: 1374576-33-6
1-[(3'S,5'R,6'S)-6'-[(hexadecoxycarbonyl)methyl]-2'-deoxy-3',5'-ethano-5',6'-methano-β-D-ribofuranosyl]thymine

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 1374576-36-9
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

Guidance literature:: With pyridine; for 23.5h; Inert atmosphere;
DOI:10.1021/jo300648u

Reference yield:

: 1374576-26-7
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

: 1374576-36-9
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

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

5: pyridine / 23.5 h / 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; potassium hydroxide; In ethanol; dichloromethane; toluene;
DOI:10.1021/jo300648u

Reference yield:

: 1374576-27-8
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

: 1374576-36-9
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

Guidance literature:: Multi-step reaction with 4 steps

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

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

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

4: pyridine / 23.5 h / Inert atmosphere

With pyridine; dmap; hydrogen fluoride; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; potassium hydroxide; In ethanol; dichloromethane;
DOI:10.1021/jo300648u