3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

Base Information

Chemical Name:3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine
CAS No.:1400908-57-7
Molecular Formula:C₃₆H₄₂N₂O₉Si
Molecular Weight:674.823
Hs Code.:

Synonyms:3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

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Technology Process of 3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

There total 9 articles about 3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)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: 89.0%

: 1400908-56-6
2'-O-acetyl-3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]thymidine

: 1400908-57-7
3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

Guidance literature:: With lithium hydroxide monohydrate; In methanol; water; at 0 - 25 ℃; for 2.5h; Inert atmosphere;
DOI:10.1055/s-0031-1289783

Reference yield:

: 1400908-55-5
2'-O-acetyl-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]thymidine

: 1400908-57-7
3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; acetonitrile / 3.5 h / 10 - 20 °C / Inert atmosphere

2: lithium hydroxide monohydrate / methanol; water / 2.5 h / 0 - 25 °C / Inert atmosphere

With lithium hydroxide monohydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1055/s-0031-1289783

Reference yield:

: 1400908-52-2
3-O-[(ethoxycarbonyl)methyl]-1,2-isopropylidene-α-D-ribofuranose

: 1400908-57-7
3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-(carboxymethyl)thymidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: dichloromethane / 0.25 h / Inert atmosphere

1.2: 1 h / 25 °C / Inert atmosphere

2.1: sulfuric acid; acetic acid / 1 h / 0 °C / Inert atmosphere

3.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 4 h / 0 - 70 °C / Inert atmosphere

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; acetonitrile / 3.5 h / 10 - 20 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / methanol; water / 2.5 h / 0 - 25 °C / Inert atmosphere

With lithium hydroxide monohydrate; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; acetonitrile; 3.1: Vorbruggen glycosylation;
DOI:10.1055/s-0031-1289783