(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

Base Information

Chemical Name:(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine
CAS No.:258505-09-8
Molecular Formula:C₃₅H₃₄F₃N₃O₈
Molecular Weight:681.665
Hs Code.:

Synonyms:(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

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Chemical Property of (3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

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Technology Process of (3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

There total 5 articles about (3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-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: 46.0%

: 239808-67-4
4,4’-dimethoxytrityl trifluoromethanesulfonate

: 258505-07-6
(3'S,5'R,6'R)-1-[2'-deoxy-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl]thymine

: 258505-09-8
(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

Guidance literature:: With pyridine; 3 A molecular sieve; at 50 ℃; for 9h;
DOI:10.1002/(SICI)1522-2675(19991110)82:11<1813::AID-HLCA1813>3.0.CO;2-0

Reference yield:

: (2S,3aS,6R,6aR)-5-Amino-6-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-3a-ol

: 258505-09-8
(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Et₃N / 1 h / 20 °C

2: 47 percent / N,O-bis(trimethylsilyl)acetamide; Me₃SiCl; Me₃SiOSO₂CF₃ / acetonitrile / 20 h / 3 °C

3: 95 percent / Bu₄NF*3H₂O; AcOH / acetonitrile / 2 h / 20 °C

4: 46 percent / 3A molecular sieves; pyridine / 9 h / 50 °C

With pyridine; chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; tetrabutyl ammonium fluoride; acetic acid; triethylamine; In acetonitrile; 1: Acylation / 2: Substitution / 3: deprotection / 4: tritylation;
DOI:10.1002/(SICI)1522-2675(19991110)82:11<1813::AID-HLCA1813>3.0.CO;2-0

Reference yield:

: (1R,3S,5S,7E/Z,8R)-8-{[(tert-butyl)dimethylsilyl]oxy}-5-hydroxy-3-methoxy-2-oxabicyclo[3.3.0]octan-6-one O-methyloxime

: 258505-09-8
(3'S,5'R,6'R)-1-{2'-deoxy-5'-O-[(4,4'-dimethoxytriphenyl)methyl]-6'-(trifluoroacetamido)-3',5'-ethano-β-D-ribofuranosyl}thymine

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / H₂; Raney-Ni; NH₃ / H₂O; ethanol / 12 h / 7500.6 Torr

2: 84 percent / Et₃N / 1 h / 20 °C

3: 47 percent / N,O-bis(trimethylsilyl)acetamide; Me₃SiCl; Me₃SiOSO₂CF₃ / acetonitrile / 20 h / 3 °C

4: 95 percent / Bu₄NF*3H₂O; AcOH / acetonitrile / 2 h / 20 °C

5: 46 percent / 3A molecular sieves; pyridine / 9 h / 50 °C

With pyridine; chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; hydrogen; nickel; acetic acid; triethylamine; In ethanol; water; acetonitrile; 1: Hydrogenation / 2: Acylation / 3: Substitution / 4: deprotection / 5: tritylation;
DOI:10.1002/(SICI)1522-2675(19991110)82:11<1813::AID-HLCA1813>3.0.CO;2-0