methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

Base Information

Chemical Name:methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose
CAS No.:651736-02-6
Molecular Formula:C₂₁H₂₃NO₅
Molecular Weight:369.417
Hs Code.:

Synonyms:methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

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Chemical Property of methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

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Technology Process of methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

There total 5 articles about methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose 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: 52.0%

: 169873-66-9
methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 651736-02-6
methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

Guidance literature:: With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane; at -78 - 20 ℃; for 7h;
DOI:10.1039/b309715n

Reference yield:

: 128657-58-9
methyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

: 651736-02-6
methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

Guidance literature:: Multi-step reaction with 3 steps

1.1: i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

1.2: tetrabutylammonium iodide / CH₂Cl₂ / 72 h

2.1: 1.06 g / tetrabutylammonium fluoride / tetrahydrofuran / 16 h

3.1: 52 percent / DMSO; (CF₃CO)2O; Et₃N / CH₂Cl₂ / 7 h / -78 - 20 °C

With tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; 3.1: Swern oxidation;
DOI:10.1039/b309715n

Reference yield:

: 651736-08-2
methyl 4,6-O-benzylidene-α-D-arabino-hexopyranoside-2-ulose Z-oxime

: 651736-02-6
methyl 2-N-benzylamino-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranoside-3-ulose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 36 percent / LiAlH₄; H₂SO₄ / tetrahydrofuran / 5 h / 20 °C

2.1: i-Pr₂NEt / CH₂Cl₂ / 3 h / 20 °C

2.2: tetrabutylammonium iodide / CH₂Cl₂ / 72 h

3.1: 1.06 g / tetrabutylammonium fluoride / tetrahydrofuran / 16 h

4.1: 52 percent / DMSO; (CF₃CO)2O; Et₃N / CH₂Cl₂ / 7 h / -78 - 20 °C

With lithium aluminium tetrahydride; sulfuric acid; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; 4.1: Swern oxidation;
DOI:10.1039/b309715n