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

Base Information

• Chemical Name: *,R^*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine
• CAS No.: 147165-81-9
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364

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

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

Chemical Property:

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

There total 5 articles about *,R^*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine 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:

allyltributylstanane (24850-33-7) + N-benzyl-1,2-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → *,R*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-81-9) + *,S*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-82-0)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 72h; diastereoselective reaction;

DOI:10.1002/ejoc.200800348

Reference yield:

allylmagnesium bromide (2622-05-1) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → *,R*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-81-9) + *,S*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-82-0)

Guidance literature:

In tetrahydrofuran; at -30 ℃; for 2h; Yield given. Yields of byproduct given;

Reference yield:

allyllithium (3052-45-7) + N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone (91190-38-4,111058-38-9,1165677-00-8) → *,R*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-81-9) + *,S*)>-N-hydroxy-2,2-dimethyl-N-(phenylmethyl)-α-(2-propenyl)-1,3-dioxolane-4-methanamine (147165-82-0)

Guidance literature:

With zinc dibromide; In diethyl ether; at -80 ℃; for 1h; Further Variations:; Reaction partners; Reagents; Solvents; Temperatures; times; Product distribution;

DOI:10.1016/j.tetlet.2006.03.004

upstream raw materials:

allylmagnesium bromide

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

allyllithium

allyltributylstanane

Downstream raw materials:

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

(2S,3S)-1-(tert-butyldiphenylsilyloxy)-3-<(phenylmethyl)amino>-5-hexen-2-ol

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

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

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