(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

Base Information

Chemical Name:(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane
CAS No.:719278-90-7
Molecular Formula:C₂₈H₂₉N₃O₄S₂
Molecular Weight:535.688
Hs Code.:

Synonyms:(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

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Chemical Property of (2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

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Technology Process of (2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

There total 12 articles about (2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane 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:

: Benzoic acid (S)-1-[(4R,5R)-5-((S)-1-azido-2-trifluoromethanesulfonyloxy-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenylsulfanyl-ethyl ester

: 108-98-5
thiophenol

: 719278-90-7
(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

Guidance literature:: With triethylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1081/NCN-120027831

Reference yield:

: (3aR,4S,6R,7R,7aR)-7-Azido-2,2-dimethyl-4-phenylsulfanylmethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

: 719278-90-7
(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.83 g / sodium borohydride / methanol / 0.5 h / -20 °C

2: imidazole / dimethylformamide / 1 h / 0 °C

3: pyridine / 12 h / 20 °C

4: 534 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

5: pyridine / CH₂Cl₂ / 0.08 h / -20 °C

6: 614 mg / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1081/NCN-120027831

Reference yield:

: 719278-88-3
(2S,3R,4S,5R)-2-azido-3,4-(dimethylmethylenedioxy)-6-phenylthio-1,5-hexanediol

: 719278-90-7
(2S,3R,4S,5R)-2-azido-5-benzoyloxy-3,4-(dimethylmethylenedioxy)-1,6-di(phenylthio)hexane

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / dimethylformamide / 1 h / 0 °C

2: pyridine / 12 h / 20 °C

3: 534 mg / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 0 °C

4: pyridine / CH₂Cl₂ / 0.08 h / -20 °C

5: 614 mg / Et₃N / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1081/NCN-120027831