<3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine

Base Information

• Chemical Name: <3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine
• CAS No.: 147165-93-3
• Molecular Formula: C₁₆H₂₂INO₃
• Molecular Weight: 403.26

Synonyms:<3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine

Chemical Property of <3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine

Chemical Property:

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Technology Process of <3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine

There total 4 articles about <3S-<3α(4R^*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine 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: 56.0%

*,R*)>-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-N-(trimethylsilyloxy)-1,3-dioxolane-4-methanamine (147165-85-3) → <3S-<3α(4R*),5α>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine (147165-92-2) + <3S-<3α(4R*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine (147165-93-3)

Guidance literature:

With N-iodo-succinimide; In chloroform; at 0 ℃; for 10h;

Reference yield: 45.0%

*,R*)>-N-(tert-butyldimethylsilyloxy)-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-83-1) → <3S-<3α(4R*),5α>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine (147165-92-2) + <3S-<3α(4R*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine (147165-93-3)

Guidance literature:

With N-iodo-succinimide; In chloroform; at 0 ℃; for 12h;

Reference yield:

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → <3S-<3α(4R*),5β>>-3-(2,2-dimethyl-1,3-dioxolan-4-yl)-5-(iodomethyl)-2-(phenylmethyl)isoxazolidine (147165-93-3)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 2 h / -30 °C

2: 70 percent / triethylamine / dimethylformamide / 4 h / 20 °C

3: 56 percent / N-iodosuccinimide (NIS) / CHCl₃ / 10 h / 0 °C

With N-iodo-succinimide; triethylamine; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

upstream raw materials:

*,R^*)>-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-N-(trimethylsilyloxy)-1,3-dioxolane-4-methanamine

*,R^*)>-N-(tert-butyldimethylsilyloxy)-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine

N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

*,R^*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine

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