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

Base Information

Chemical Name:methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside
CAS No.:1394848-34-0
Molecular Formula:C₂₃H₂₆F₃NO₅
Molecular Weight:453.458
Hs Code.:

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

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Chemical Property of methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside

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Technology Process of methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside

There total 4 articles about methyl 3,5-di-O-benzyl-2-deoxy-2-α-[(α,α,α-trifluoroacetyl)aminomethyl]-α-D-ribofuranoside 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: 68.0%

: 383-64-2
S-ethyl trifluoroacetate

: 1394848-33-9
methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside

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

Guidance literature:: methyl 3,5-di-O-benzyl-2-deoxy-2-α-phthalimidomethyl-α-D-ribofuranoside; With methylamine; In ethanol; at 80 ℃; for 2.5h; Sealed tube;

S-ethyl trifluoroacetate; With triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1039/c2cc34556k

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: 1394848-32-8
methyl 3,5-di-O-benzyl-2-methylene-α-D-ribofuranoside

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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C

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

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

3.2: 1 h / 20 °C

With 9-borabicyclo[3.3.1]nonane dimer; triphenylphosphine; methylamine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; 1.1: Hydroboration reaction / 2.1: Mitsunobu reaction;
DOI:10.1039/c2cc34556k