3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

Base Information

Chemical Name:3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine
CAS No.:1394848-39-5
Molecular Formula:C₂₆H₂₆F₃N₃O₆
Molecular Weight:533.504
Hs Code.:

Synonyms:3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

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Chemical Property of 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

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Technology Process of 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

There total 5 articles about 3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine 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: 65.0%

: 1394848-34-0
methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside

: 3442-82-8
1,3-bis(trimethylsilyl)uracil

: 1394848-39-5
3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

Guidance literature:: methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside; 1,3-bis(trimethylsilyl)uracil; With tin(IV) chloride; In acetonitrile; at 20 ℃; for 3.5h; Inert atmosphere;

With water; sodium hydrogencarbonate; In acetonitrile; for 0.25h; diastereoselective reaction;
DOI:10.1039/c2cc34556k

Reference yield:

: 885592-69-8
(2S,4R,5R)-4-(benzyloxy)-5-((benzyloxy)methyl)-2-methoxydihydrofuran-3(2H)-one

: 1394848-39-5
3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

Guidance literature:: Multi-step reaction with 5 steps

1.1: sec.-butyllithium / tetrahydrofuran; cyclohexane / 1 h / -78 °C / Inert atmosphere

1.2: 72 h / -78 - 20 °C / Inert atmosphere

2.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2.2: 2 h / 20 °C

3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

4.1: methylamine / ethanol / 2.5 h / 80 °C / Sealed tube

4.2: 1 h / 20 °C

5.1: tin(IV) chloride / acetonitrile / 3.5 h / 20 °C / Inert atmosphere

5.2: 0.25 h

With 9-borabicyclo[3.3.1]nonane dimer; sec.-butyllithium; tin(IV) chloride; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; cyclohexane; acetonitrile; 1.2: Wittig reaction / 2.1: Hydroboration reaction / 3.1: Mitsunobu reaction;
DOI:10.1039/c2cc34556k

Reference yield:

: 1394848-29-3
methyl 3,5-di-O-benzyl-2-deoxy-2-α-hydroxymethyl-α-D-ribofuranoside

: 1394848-39-5
3',5'-di-O-benzyl-2'-deoxy-2'-C-α-[( α, α, α-trifluoroacetyl)aminomethyl]uridine

Guidance literature:: Multi-step reaction with 3 steps

1.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.1: methylamine / ethanol / 2.5 h / 80 °C / Sealed tube

2.2: 1 h / 20 °C

3.1: tin(IV) chloride / acetonitrile / 3.5 h / 20 °C / Inert atmosphere

3.2: 0.25 h

With tin(IV) chloride; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; acetonitrile; 1.1: Mitsunobu reaction;
DOI:10.1039/c2cc34556k