(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

Base Information

Chemical Name:(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol
CAS No.:151765-54-7
Molecular Formula:C₂₈H₃₀O₅
Molecular Weight:446.543
Hs Code.:

Synonyms:(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

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Chemical Property of (1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

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Technology Process of (1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

There total 9 articles about (1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol 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: 95.0%

: 161596-04-9
(1R,2R,3R,4R)-2,3-di-O-benzyl-4-benzyloxymethylcyclohex-5-ene-1,2,3-triol

: 151765-54-7
(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 36h; Ambient temperature;
DOI:10.1039/c39930000995

Reference yield:

: 135735-91-0
(1R,2R,3S,4R,5R)-3-O-Benzyl-5-benzyloxymethyl-1,2-O-cyclohexylidene-cyclohexan-1,2,3,4-tetraol

: 151765-54-7
(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH, 2.) n-Bu₄NI / 1.) THF, 0 deg C, 2.) THF, reflux, overnight

2: 90 percent / CF₃CO₂H / CH₂Cl₂ / 24 h / Ambient temperature

3: 1.) triethylamine, thionyl chloride, 2.) NaIO₄, RuCl₃, / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, CCl₄, MeCN, H₂O, from 0 deg C to RT, 1 h

4: 1.) sodium borohydride, 2.) aq. H₂SO₄ / 1.) EtOH, 0 deg C, 2.) EtOH

5: 1.) MCPBA, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -40 deg C, 2.) toluene

6: 96 percent / N,N-dimethylaminopyridine, pyridine / CH₂Cl₂ / 24 h / Ambient temperature

7: MCPBA / CH₂Cl₂ / 42 h / Heating

8: potassium carbonate / methanol / 24 h / Ambient temperature

With pyridine; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1039/c39930000995

Reference yield:

: 151693-58-2
(1R,2R,3S,4R,5R)-3,4-di-O-benzyl-5-benzyloxymethylcyclohexane-1,2,3,4-tetraol

: 151765-54-7
(1S,2S,3R,4R,5R,6R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-7-oxabicyclo[4.1.0]heptan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) triethylamine, thionyl chloride, 2.) NaIO₄, RuCl₃, / 1.) CH₂Cl₂, 0 deg C, 5 min, 2.) CH₂Cl₂, CCl₄, MeCN, H₂O, from 0 deg C to RT, 1 h

2: 1.) sodium borohydride, 2.) aq. H₂SO₄ / 1.) EtOH, 0 deg C, 2.) EtOH

3: 1.) MCPBA, 2.) i-Pr₂NEt / 1.) CH₂Cl₂, -40 deg C, 2.) toluene

4: 96 percent / N,N-dimethylaminopyridine, pyridine / CH₂Cl₂ / 24 h / Ambient temperature

5: MCPBA / CH₂Cl₂ / 42 h / Heating

6: potassium carbonate / methanol / 24 h / Ambient temperature

With pyridine; dmap; ruthenium trichloride; sodium tetrahydroborate; sodium periodate; thionyl chloride; sulfuric acid; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1039/c39930000995