Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester
CAS No.:471930-68-4
Molecular Formula:C₂₄H₂₆Cl₃NO₇
Molecular Weight:546.832
Hs Code.:

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester 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: 91.0%

: 471930-67-3
dimethylthexylsilyl 3-O-acetyl-4,6-di-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

: 471930-68-4
Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 20h;
DOI:10.1021/jo025834+

Reference yield:

: 81928-98-5
4,6-di-O-benzyl-D-galactal

: 471930-68-4
Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / pyridine

2.1: CAN; NaN₃ / acetonitrile / 4 h / -15 °C

2.2: thiophenol; diisopropylethylamine / acetonitrile / 1.5 h / 0 °C

2.3: 1.48 g / imidazole / dimethylformamide / 12 h / 20 °C

3.1: sodium borohydride; NiCl₂ / ethanol / 1.5 h / 20 °C

3.2: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

3.3: 40 percent / pyridine / 12 h

4.1: 91 percent / tetrabutylammonium fluoride; AcOH / tetrahydrofuran / 20 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; acetic acid; nickel dichloride; In tetrahydrofuran; ethanol; acetonitrile;
DOI:10.1021/jo025834+

Reference yield:

: 100-39-0
benzyl bromide

: 471930-68-4
Acetic acid (2R,3R,4R,5R,6R)-3-benzyloxy-2-benzyloxymethyl-6-hydroxy-5-(2,2,2-trichloro-acetylamino)-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 36 percent / sodium hydride / dimethylformamide / 0 °C

2.1: 97 percent / pyridine

3.1: CAN; NaN₃ / acetonitrile / 4 h / -15 °C

3.2: thiophenol; diisopropylethylamine / acetonitrile / 1.5 h / 0 °C

3.3: 1.48 g / imidazole / dimethylformamide / 12 h / 20 °C

4.1: sodium borohydride; NiCl₂ / ethanol / 1.5 h / 20 °C

4.2: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4.3: 40 percent / pyridine / 12 h

5.1: 91 percent / tetrabutylammonium fluoride; AcOH / tetrahydrofuran / 20 h / 20 °C

With pyridine; sodium tetrahydroborate; sodium azide; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; sodium hydride; acetic acid; nickel dichloride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo025834+