(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

Base Information

Chemical Name:(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one
CAS No.:1377616-69-7
Molecular Formula:C₁₈H₂₀INO₄
Molecular Weight:441.266
Hs Code.:

Synonyms:(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

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Chemical Property of (3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

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Technology Process of (3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

There total 4 articles about (3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one 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: 87.0%

: S-methyl (1S,5S,6S)-O-[5,6-(isopropylidenedioxy)-4-methylene-2-cyclohexenyl]N-benzylcarbonimidothioate

: 1377616-69-7
(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

Guidance literature:: With iodine; potassium carbonate; In tetrahydrofuran; at 25 ℃; for 18h; Inert atmosphere;
DOI:10.1002/ejoc.201101845

Reference yield:

: 622-78-6
Benzyl isothiocyanate

: 1377616-69-7
(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 25 °C / Inert atmosphere

1.3: 25 °C / Inert atmosphere

2.1: iodine; potassium carbonate / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere

With iodine; sodium hydride; potassium carbonate; In tetrahydrofuran;
DOI:10.1002/ejoc.201101845

Reference yield:

: 1377616-64-2
(4S,5R,6S)-4-hydroxy-5,6-(isopropylidenedioxy)cyclohex-2-en-1-one

: 1377616-69-7
(3aS,6R,7S,7aS)-3-benzyl-3a,6,7,7a-tetrahydro-5-iodomethyl-6,7-(isopropylidenedioxy)benzoxazol-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 - 25 °C / Inert atmosphere

2.3: 25 °C / Inert atmosphere

3.1: iodine; potassium carbonate / tetrahydrofuran / 18 h / 25 °C / Inert atmosphere

With n-butyllithium; iodine; sodium hydride; potassium carbonate; In tetrahydrofuran; hexane;
DOI:10.1002/ejoc.201101845