(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

Base Information

Chemical Name:(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime
CAS No.:214041-53-9
Molecular Formula:C₂₈H₂₉NO₆
Molecular Weight:475.541
Hs Code.:

Synonyms:(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

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Chemical Property of (2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

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Technology Process of (2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

There total 6 articles about (2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime 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:

: 214041-46-0
[2R-(2α,3β,4α,5β)]-2-(acetyloxy)-1-(O-methyloxime)-3,6-O-benzylidene-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)cyclopentanone

: 214041-53-9
(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 0.5h;
DOI:10.1021/jo980485y

Reference yield:

: 20770-84-7,113566-69-1,113566-70-4
2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose

: 214041-53-9
(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

Guidance literature:: Multi-step reaction with 6 steps

1: 3.52 g / pyridine / 24 h / 40 - 45 °C

2: 1.14 g / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

3: 84 percent / t-BuOH; SmI₂ / tetrahydrofuran / -78 - 20 °C

4: 1.78 g / pyridine; DMAP / 20 °C

5: 44 percent / Pb(OAc)4 / benzene / 40 h / 20 - 40 °C

6: 88 mg / K₂CO₃ / methanol / 0.5 h / 20 °C

With pyridine; lead(IV) acetate; dmap; samarium diiodide; potassium carbonate; Dess-Martin periodane; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; benzene; 1: Condensation / 2: Dess-Martin oxidation / 3: Cyclization / 4: Acetylation / 5: Oxidation / 6: Deacetylation;
DOI:10.1021/jo980485y

Reference yield:

: 4,6-O-benzylidene-2,3-O-bis(phenylmethyl)-1-(O-methyloxime)-D-xylo-hexos-5-ulose

: 214041-53-9
(2R,4aR,6S,7R,7aS)-6,7-Bis-benzyloxy-4a-hydroxy-2-phenyl-tetrahydro-cyclopenta[1,3]dioxin-5-one O-methyl-oxime

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / t-BuOH; SmI₂ / tetrahydrofuran / -78 - 20 °C

2: 1.78 g / pyridine; DMAP / 20 °C

3: 44 percent / Pb(OAc)4 / benzene / 40 h / 20 - 40 °C

4: 88 mg / K₂CO₃ / methanol / 0.5 h / 20 °C

With pyridine; lead(IV) acetate; dmap; samarium diiodide; potassium carbonate; tert-butyl alcohol; In tetrahydrofuran; methanol; benzene; 1: Cyclization / 2: Acetylation / 3: Oxidation / 4: Deacetylation;
DOI:10.1021/jo980485y