N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

Base Information

Chemical Name:N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide
CAS No.:177361-86-3
Molecular Formula:C₃₀H₃₁F₃N₄O₆
Molecular Weight:600.595
Hs Code.:

Synonyms:N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

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Chemical Property of N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

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Technology Process of N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

There total 6 articles about N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide 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: 86.0%

: 2746-25-0
p-Methoxybenzyl bromide

: 177361-90-9
N-((2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-3-yl)-2,2,2-trifluoro-acetamide

: 177361-86-3
N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 6h;
DOI:10.1080/07328309608005660

Reference yield:

: 13347-83-6
benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside

: 177361-86-3
N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 12 h

2: 89 percent / pyridine / 0 °C

3: 52 percent / NaN₃, Bu₄NHSO₄ / dimethylformamide / 36 h / 80 °C

4: 78 percent / TFA, Et₃SiH / CH₂Cl₂ / 1.) 0 deg C to r.t., 2.) r.t., 24 h

5: 86 percent / NaH / tetrahydrofuran / 6 h

With pyridine; triethylsilane; sodium azide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005660

Reference yield:

: 13343-63-0
benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

: 177361-86-3
N-[(2S,3R,4R,5S,6R)-4-Azido-2-benzyloxy-6-benzyloxymethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl]-2,2,2-trifluoro-acetamide

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / 90percent NH₂NH₂*H₂O / 12 h / 130 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 12 h

3: 89 percent / pyridine / 0 °C

4: 52 percent / NaN₃, Bu₄NHSO₄ / dimethylformamide / 36 h / 80 °C

5: 78 percent / TFA, Et₃SiH / CH₂Cl₂ / 1.) 0 deg C to r.t., 2.) r.t., 24 h

6: 86 percent / NaH / tetrahydrofuran / 6 h

With pyridine; triethylsilane; sodium azide; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; hydrazine hydrate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1080/07328309608005660