(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

Base Information

Chemical Name:(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate
CAS No.:935398-10-0
Molecular Formula:C₁₅H₁₈O₄
Molecular Weight:262.306
Hs Code.:

Synonyms:(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

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Chemical Property of (1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

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Technology Process of (1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

There total 6 articles about (1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate 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%

: (R)-4-(benzyloxy)-3,4-dihydro-2H-pyran

: 6832-16-2
methyl diazoacetate

: 935398-10-0
(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

Guidance literature:: dirhodium tetraacetate; In dichloromethane; at 23 ℃;
DOI:10.1021/ol070177z

Reference yield:

: 83122-90-1
1,2-dideoxy-4,6-O-isopropylidine-D-glucopyranose

: 935398-10-0
(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 6 h / 0 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 0.75 h

4.1: N,N-dimethylformamide dineopentyl acetal / toluene / 1 h / 120 °C / Inert atmosphere

5.1: dirhodium tetraacetate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

With dirhodium tetraacetate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydride; toluene-4-sulfonic acid; N,N-dimethylformamide dineopentyl acetal; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2012.03.021

Reference yield:

: 1374115-48-6
1,2-dideoxy-3-O-benzyl-4,6-O-isopropylidene-β-D-glucose

: 935398-10-0
(1R,5R,6S)-methyl 5-(benzyloxy)-2-oxabicyclo[4.1.0]heptane-(7R)-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C / Inert atmosphere

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 0.75 h

3: N,N-dimethylformamide dineopentyl acetal / toluene / 1 h / 120 °C / Inert atmosphere

4: dirhodium tetraacetate / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

With dirhodium tetraacetate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; toluene-4-sulfonic acid; N,N-dimethylformamide dineopentyl acetal; In methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2012.03.021