(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

Base Information

Chemical Name:(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester
CAS No.:168039-37-0
Molecular Formula:C₂₇H₂₈O₁₁
Molecular Weight:528.513
Hs Code.:

(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

Synonyms:(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

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Chemical Property of (3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

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Technology Process of (3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

There total 7 articles about (3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester 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: 76.0%

: 167964-35-4
<4R,4(1S),5R,8S,9S>-9-Hydroxy-4--2,2-dimethyl-6-oxo-1,3,7-trioxaspiro<4.4>nonan-8,9-dicarboxylic acid bis(phenylmethyl) ester

: 168039-37-0
(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

Guidance literature:: With mercury(II) perchlorate; water; calcium carbonate; In tetrahydrofuran; at 25 ℃; for 2h;

Reference yield:

: 9-Hydroxy-4--2,2-dimethyl-6-oxo-1,3,7-trioxaspiro<4.4>nonan-8,9-dicarboxylic acid bis(phenylmethyl) ester

: 168039-37-0
(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

: (3aS,4R,5S,6aR,7R,9aS)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

Guidance literature:: With mercury(II) perchlorate; calcium carbonate; In tetrahydrofuran; at 22 ℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield:

: 167964-31-0
(4R,5R,8R,9S)-9-Hydroxy-8,9-bis(hydroxymethyl)-2,2-dimethyl-4-<<<2-(trimethylsilyl)ethoxy>methoxy>methyl>-1,3,7-trioxaspiro<4.4>nonan-6-one

: 168039-37-0
(3aR,4S,5R,6aS,7S,9aR)-Dihydro-4,5-dihydroxy-2,2,5-trimethyl-9-oxo-5H,9H-1,3-dioxolo<4,5-c>furo<3,4-b>pyran-6a,7(7H)-dicarboxylic acid bis(phenylmethyl) ester

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / imidazole, 4-dimethylaminopyridine / dimethylformamide / 40 h / 25 °C

3: 2.) pyridine, p-TosOH / 1.) 90 deg C, 1h, 2.) CH₂Cl₂, MeOH, 25 deg C, 5 min

4: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

5: 1.) BuLi / 1.) THF, -23 deg C, 1.5 h, 2.) THF, -78 deg C, 1 h

6: 76 percent / Hg(ClO₄)2, CaCO₃, H₂O / tetrahydrofuran / 2 h / 25 °C

With pyridine; 1H-imidazole; dmap; n-butyllithium; mercury(II) perchlorate; water; Dess-Martin periodane; toluene-4-sulfonic acid; calcium carbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;