(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

Base Information

Chemical Name:(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine
CAS No.:1370411-86-1
Molecular Formula:C₃₉H₄₈N₂O₈Si
Molecular Weight:700.904
Hs Code.:

Synonyms:(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

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Chemical Property of (3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

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Technology Process of (3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

There total 10 articles about (3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine 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: 90.0%

: 1370411-85-0
(3'S,5'R)-1-[3',5'-dihydroxy-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

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

: 1370411-86-1
(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

Guidance literature:: With pyridine; at 20 ℃; for 5h; Inert atmosphere;
DOI:10.1021/jo300554w

Reference yield:

: C₂₁H₂₄O₅

: 1370411-86-1
(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine / 16 h / 20 °C / Inert atmosphere

2.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 1 h / 80 °C / Inert atmosphere

2.2: 16 h / 0 - 50 °C / Inert atmosphere

3.1: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

4.1: bis(phenyl) carbonate; sodium hydrogencarbonate / N,N-dimethyl-formamide / 1 h / 150 °C / Inert atmosphere

5.1: potassium hydroxide / Reflux; Inert atmosphere

6.1: N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

7.1: 20% palladium hydroxide on charcoal; hydrogen; cyclohexa-1,3-diene / ethyl acetate / 2 h / 20 °C

8.1: pyridine / 5 h / 20 °C / Inert atmosphere

With pyridine; bis(phenyl) carbonate; N,O-bis-(trimethylsilyl)-acetamide; 20% palladium hydroxide on charcoal; hydrogen; sodium methylate; sodium hydrogencarbonate; cyclohexa-1,3-diene; potassium hydroxide; In methanol; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo300554w

Reference yield:

: 1370411-72-5
(3'S,5'R)-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)thymidine

: 1370411-86-1
(3'S,5'R)-1-[3'-hydroxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-(tert-butyldimethylsilyl)-3',5'-ethano-β-D-arabinofuranosyl]thymidine

Guidance literature:: Multi-step reaction with 6 steps

1: sodium methylate / methanol / 4 h / 20 °C / Inert atmosphere

2: bis(phenyl) carbonate; sodium hydrogencarbonate / N,N-dimethyl-formamide / 1 h / 150 °C / Inert atmosphere

3: potassium hydroxide / Reflux; Inert atmosphere

4: N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

5: 20% palladium hydroxide on charcoal; hydrogen; cyclohexa-1,3-diene / ethyl acetate / 2 h / 20 °C

6: pyridine / 5 h / 20 °C / Inert atmosphere

With pyridine; bis(phenyl) carbonate; 20% palladium hydroxide on charcoal; hydrogen; sodium methylate; sodium hydrogencarbonate; cyclohexa-1,3-diene; potassium hydroxide; In methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo300554w