(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

Base Information

Chemical Name:(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil
CAS No.:1332758-23-2
Molecular Formula:C₂₃H₃₁IN₂O₅Si
Molecular Weight:570.5
Hs Code.:

Synonyms:(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

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Chemical Property of (E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

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Technology Process of (E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

There total 7 articles about (E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil 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: 53.0%

: 1332758-18-5
3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-β-D-ribopentofuranosyl]uracil

: 1332758-25-4
C₂₃H₃₁IN₂O₅Si

: 1332758-19-6
(Z)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

: 1332758-23-2
(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

Guidance literature:: With iodoniumdicollidinium triflate; In acetonitrile; at -20 ℃; for 0.5h;
DOI:10.1021/jo202159q

Reference yield:

: 1332758-16-3
3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3-deoxy-β-D-ribo-pentofuranosyl]uracil

: 1332758-25-4
C₂₃H₃₁IN₂O₅Si

: 1332758-19-6
(Z)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

: 1332758-23-2
(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole; iodine; triphenylphosphine / tetrahydrofuran / 3.17 h / 0 - 20 °C / Inert atmosphere

2: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

3: iodonium di(2,4,6-collidinium) triflate / dichloromethane

With 1H-imidazole; iodonium di(2,4,6-collidinium) triflate; iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol202124b

Reference yield:

: 1332758-17-4
3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

: 1332758-25-4
C₂₃H₃₁IN₂O₅Si

: 1332758-19-6
(Z)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

: 1332758-23-2
(E)-3-(benzyloxymethyl)-1-[2-O-(tert-butyldimethylsilyl)-4,5-didehydro-3,5-dideoxy-5-iodo-β-D-ribopentofuranosyl]uracil

Guidance literature:: Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 0 - 20 °C / Inert atmosphere

2: iodonium di(2,4,6-collidinium) triflate / dichloromethane

With iodonium di(2,4,6-collidinium) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile;
DOI:10.1021/ol202124b