(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

Base Information

Chemical Name:(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol
CAS No.:171252-90-7
Molecular Formula:C₂₅H₂₉N₃O₇
Molecular Weight:483.521
Hs Code.:

Synonyms:(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

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Chemical Property of (1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

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Technology Process of (1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

There total 7 articles about (1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol 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: 60.0%

: 171252-89-4
(1R,2S,3R,4S,5S)-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)-1-O-(trifluoromethanesulfonyl)cyclohexane-1,2,3,4,5-pentol

: 171252-90-7
(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

Guidance literature:: With sodium azide; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; In N,N-dimethyl-formamide;

Reference yield:

: 135735-90-9
(1R,2R,3S)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohex-4-en-1,2,3-triol

: 171252-90-7
(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / Me₃NO, OsO₄ / 2-methyl-propan-2-ol; pyridine; H₂O / 12 h / Heating

2: 90 percent / DMAP / triethylamine / 3 h / Heating

3: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

4: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5: 60 percent / NaN₃, benzo-15-crown-5 / dimethylformamide / Ambient temperature

With pyridine; dmap; osmium(VIII) oxide; sodium azide; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; trimethylamine-N-oxide; water; trifluoroacetic acid; In pyridine; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo9607828

Reference yield:

: 183268-55-5
(1R,2R,3S,4S,5S)-3-O-benzyl-5-((benzyloxy)methyl)-1,2-O-cyclohexylidenecyclohexane-1,2,3,4,5-pentol

: 171252-90-7
(1S,2R,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / DMAP / triethylamine / 3 h / Heating

2: 90 percent / TFA, H₂O / CH₂Cl₂ / 24 h / Ambient temperature

3: 93 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

4: 60 percent / NaN₃, benzo-15-crown-5 / dimethylformamide / Ambient temperature

With pyridine; dmap; sodium azide; 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin; water; trifluoroacetic acid; In dichloromethane; triethylamine; N,N-dimethyl-formamide;
DOI:10.1021/jo9607828