4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Base Information

Chemical Name:4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine
CAS No.:583829-89-4
Molecular Formula:C₄₁H₄₃N₃O₇Si
Molecular Weight:717.894
Hs Code.:

Synonyms:4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

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Chemical Property of 4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

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Technology Process of 4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

There total 5 articles about 4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine 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: 70.0%

: 583829-88-3
4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-4'-C-hydroxymethyl-cytidine

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 583829-89-4
4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: With toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 60 ℃; for 1.5h;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 583829-86-1
4-C-acetoxymethyl-1,2-di-O-acetyl-3-O-benzyl-5-O-tert-butyldiphenylsilyl-D-erythro-pentofuranose

: 583829-89-4
4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: Multi-step reaction with 3 steps

1: 76 percent / N,O-bis(trimethylsilyl)acetamide; TMSOTf / acetonitrile / 1 h / Heating

2: 84 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

3: 70 percent / TsOH*H₂O / 1,2-dichloro-ethane / 1.5 h / 60 °C

With lithium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; water; 1,2-dichloro-ethane; acetonitrile; 1: Vorbrueggen reaction;
DOI:10.1016/j.bmc.2005.09.020

Reference yield:

: 583829-87-2
4'-C-acetoxymethyl-2'-O-acetyl-4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-cytidine

: 583829-89-4
4-N-benzoyl-3'-O-benzyl-5'-O-tert-butyldiphenylsilyl-2'-O,4'-C-(methylenoxymethylene)cytidine

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 2 h / 20 °C

2: 70 percent / TsOH*H₂O / 1,2-dichloro-ethane / 1.5 h / 60 °C

With lithium hydroxide; toluene-4-sulfonic acid; In tetrahydrofuran; water; 1,2-dichloro-ethane;
DOI:10.1016/j.bmc.2005.09.020