(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

Base Information

Chemical Name:(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol
CAS No.:183505-15-9
Molecular Formula:C₂₁H₂₅N₃O₅
Molecular Weight:399.447
Hs Code.:

Synonyms:(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

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Chemical Property of (1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

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Technology Process of (1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

There total 11 articles about (1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol 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: 88.0%

: 171339-42-7
(1R,2S,3R,4S,5S)-1-azido-4,5-di-O-acetyl-3-O-benzyl-5-((benzyloxy)methyl)cyclohexane-2,3,4,5-tetrol

: 183505-15-9
(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

Guidance literature:: With potassium carbonate; In methanol; for 1.5h; Ambient temperature;
DOI:10.1021/jo9607828

Reference yield: 80.0%

: 183268-67-9
Acetic acid (1S,2S,4R,5S,6R)-5-acetoxy-4-azido-6-benzyloxy-2-benzyloxymethyl-2-hydroxy-cyclohexyl ester

: 183505-15-9
(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

Guidance literature:: With potassium carbonate; In methanol; for 24h; Ambient temperature;
DOI:10.1021/jo9607828

Reference yield:

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

: 183505-15-9
(1S,2S,3R,4S,5R)-5-Azido-3-benzyloxy-1-benzyloxymethyl-cyclohexane-1,2,4-triol

Guidance literature:: Multi-step reaction with 8 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: 1.) 1,1'-(thiocarbonyl)diimidazole, 2.) P(OMe)3 / 1.) toluene, 90 deg C, 1.5 h; reflux, overnight, 2.) reflux, 24 h

5: 81 percent / NaIO₄, RuCl₃*H₂O / CCl₄; acetonitrile; H₂O / 0 °C / Heating

6: 1.) Et₃N, SOCl₂, 2.) RuCl₃*H₂O, NaIO₄ / 1.) CH₂Cl₂, 0 deg C, 2.) CCl₄, CH₃CN, H₂O, 0 deg C, 1 h

7: 1.) LiN₃, 2.) 20percent H₂SO₄ / 1.) DMF, room temperature, 6 h, 2.) THF, 1 h

8: 88 percent / K₂CO₃ / methanol / 1.5 h / Ambient temperature

With dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; thionyl chloride; lithium azide; trimethylamine-N-oxide; sulfuric acid; water; potassium carbonate; triethylamine; 1,1'-Thiocarbonyldiimidazole; trifluoroacetic acid; phosphorous acid trimethyl ester; In pyridine; methanol; tetrachloromethane; dichloromethane; water; triethylamine; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo9607828