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

Base Information

Chemical Name:2'-O-acetyl-3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]thymidine
CAS No.:1400908-56-6
Molecular Formula:C₄₀H₄₈N₂O₁₀Si
Molecular Weight:744.914
Hs Code.:

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

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Chemical Property of 2'-O-acetyl-3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]thymidine

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Technology Process of 2'-O-acetyl-3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]thymidine

There total 8 articles about 2'-O-acetyl-3-N-(benzyloxymethyl)-5'-O-(tert-butyldiphenylsilyl)-3'-O-[(ethoxycarbonyl)methyl]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: 73.0%

: 3587-60-8
Benzyloxymethyl chloride

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

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

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; at 10 - 20 ℃; for 3.5h; Inert atmosphere;
DOI:10.1055/s-0031-1289783

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 1400908-54-4
5-O-(tert-butyldiphenylsilyl)-3-O-[(ethoxycarbonyl)methyl]-1,2-isopropylidene-α-D-ribofuranose

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane; acetonitrile / 3.5 h / 10 - 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; 2: Vorbruggen glycosylation;
DOI:10.1055/s-0031-1289783