(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

Base Information

Chemical Name:(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene
CAS No.:725253-60-1
Molecular Formula:C₂₈H₃₅IO₇
Molecular Weight:610.486
Hs Code.:

Synonyms:(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

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Chemical Property of (3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

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Technology Process of (3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

There total 7 articles about (3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene 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: 92.0%

: 725253-41-8
[(3aS,4aS,6R,7R,8R,8aS,10aR)-8-Benzyloxy-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulen-6-yl]-methanol

: 725253-60-1
(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

Guidance literature:: With 1H-imidazole; iodine; triphenylphosphine; In tetrahydrofuran; at 20 ℃;
DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

: 252046-22-3
(2R,3R,4S,4aS,9aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-2,3,4,4a,9,9a-hexahydro-6H-pyrano[3,2-b]oxepin

: 725253-60-1
(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

Guidance literature:: Multi-step reaction with 7 steps

1: AD-mix β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O; various solvent(s) / 0 °C

2: CSA / CH₂Cl₂ / 20 °C

3: H₂ / Pd/C / ethyl acetate; methanol / 20 °C

4: CSA / CH₂Cl₂ / 20 °C

5: 92 percent / KOt-Bu; n-Bu₄NI / tetrahydrofuran / 20 °C

6: 100 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

7: 92 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

With 1H-imidazole; methanesulfonamide; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1016/j.tetlet.2004.04.083

Reference yield:

: 725253-39-4
(3aS,4aS,6R,7R,8R,8aS,10aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

: 725253-60-1
(3aS,4aS,6S,7S,8R,8aS,10aR)-8-Benzyloxy-6-iodomethyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-octahydro-1,3,5,9-tetraoxa-benzo[f]azulene

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd/C / ethyl acetate; methanol / 20 °C

2: CSA / CH₂Cl₂ / 20 °C

3: 92 percent / KOt-Bu; n-Bu₄NI / tetrahydrofuran / 20 °C

4: 100 percent / DIBAL-H / CH₂Cl₂ / -78 - 0 °C

5: 92 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 20 °C

With 1H-imidazole; camphor-10-sulfonic acid; potassium tert-butylate; hydrogen; iodine; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/j.tetlet.2004.04.083