9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

Base Information

Chemical Name:9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine
CAS No.:1226528-07-9
Molecular Formula:C₂₁H₂₄N₆O₃Si
Molecular Weight:436.545
Hs Code.:

Synonyms:9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

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Chemical Property of 9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

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Technology Process of 9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

There total 4 articles about 9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine 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: 38.0%

: C₁₄H₂₀N₆O₂Si

: 98-88-4
benzoyl chloride

: 1226528-07-9
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

: 1226528-11-5
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-4-benzoylcytosine

Guidance literature:: In pyridine; at 20 ℃; for 8h;
DOI:10.1016/j.tetlet.2010.02.046

Reference yield:

: C₁₅H₂₂N₂O₄Si

: 1226528-07-9
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

: 1226528-11-5
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-4-benzoylcytosine

Guidance literature:: Multi-step reaction with 3 steps

1.1: methanesulfonyl chloride; pyridine / 0 - 20 °C

1.2: 100 °C

2.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / Reflux

3.1: pyridine / 10 h / 20 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; methanesulfonyl chloride; In 1,2-dichloro-ethane;
DOI:10.1002/anie.201404797

Reference yield:

: 3,5-anhydro-2-deoxy-β-D-threo-pentofuranosyl-1-thymine

: 1226528-07-9
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-α-D-ribofuranosyl)-4-benzoylcytosine

: 1226528-11-5
9-(3'-azido-2',3',5'-trideoxy-5'-(trimethylsilyl)ethynyl-β-D-ribofuranosyl)-4-benzoylcytosine

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium; boron trifluoride diethyl etherate / tetrahydrofuran / 16 h / -78 °C

2.1: methanesulfonyl chloride; pyridine / 0 - 20 °C

2.2: 100 °C

3.1: trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / 3 h / Reflux

4.1: pyridine / 10 h / 20 °C

With pyridine; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; methanesulfonyl chloride; In tetrahydrofuran; 1,2-dichloro-ethane;
DOI:10.1002/anie.201404797