6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

Base Information

Chemical Name:6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose
CAS No.:666238-07-9
Molecular Formula:C₂₅H₂₇NO₇
Molecular Weight:453.492
Hs Code.:

Synonyms:6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

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Chemical Property of 6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

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Technology Process of 6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

There total 7 articles about 6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose 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: 58.0%

: 143-33-9,25596-52-5
sodium cyanide

: 666238-01-3
2,6-di-O-acetyl-3,4-di-O-benzyl-α-D-glucopyranosyl bromide

: 666238-07-9
6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

: 6-O-acetyl-3,4-di-O-benzyl-[(R)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

Guidance literature:: With tetrabutylammomium bromide; In acetonitrile; at 20 ℃; for 20h;
DOI:10.1081/CAR-120026603

Reference yield:

: 97673-01-3
1,2-O-<1-(exo-ethoxy)ethylidene>-α-D-glucopyranose

: 666238-07-9
6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 6 steps

1.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / 20 °C

2.1: sodium hydride / dimethylformamide / 0.5 h / 0 °C

2.2: 71 percent / dimethylformamide / 2 h / 20 °C

3.1: 96 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.5 h / 20 °C

4.1: 80 percent / pyridine / 0.5 h / 20 °C

5.1: acetyl bromide; tetraethylammonium bromide / CH₂Cl₂ / 0.5 h / 20 °C

6.1: 58 percent / tetrabutylammonium bromide / acetonitrile / 20 h / 20 °C

With pyridine; dmap; Acetyl bromide; tetraethylammonium bromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/CAR-120026603

Reference yield:

: 100-39-0
benzyl bromide

: 666238-07-9
6-O-acetyl-3,4-di-O-benzyl-[(S)-1,2-O-(1-cyanoethylidene)]-α-D-glucopyranose

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / dimethylformamide / 0.5 h / 0 °C

1.2: 71 percent / dimethylformamide / 2 h / 20 °C

2.1: 96 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 0.5 h / 20 °C

3.1: 80 percent / pyridine / 0.5 h / 20 °C

4.1: acetyl bromide; tetraethylammonium bromide / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 58 percent / tetrabutylammonium bromide / acetonitrile / 20 h / 20 °C

With pyridine; Acetyl bromide; tetraethylammonium bromide; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1081/CAR-120026603