<4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine

Base Information

• Chemical Name: <4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine
• CAS No.: 105369-31-1
• Molecular Formula: C₁₆H₂₃NO₃
• Molecular Weight: 277.364

Synonyms:<4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine

Chemical Property of <4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine

Chemical Property:

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Technology Process of <4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine

There total 10 articles about <4S-<4α,4(R^*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-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: 91.0%

N-<1-<<4S-<4α,4(R*),5β>>-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenyl>-2,2,2-trichloroacetamide (105281-23-0,105369-30-0) → <4S-<4α,4(R*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine (105369-31-1)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 4h;

DOI:10.1021/jo00375a057

Reference yield: 82.0%

N-<1-<<4S-<4α,4(S*),5β>>-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenyl>-2,2,2-trichloroacetamide (105281-23-0,105369-30-0) → <4S-<4α,4(S*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine (105281-24-1,105369-31-1)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 60 ℃; for 4h;

DOI:10.1021/jo00375a057

Reference yield:

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde (81028-12-8) → <4S-<4α,4(S*),5β>>-2,2-dimethyl-α-ethenyl-5-<(phenylmethoxy)methyl>-1,3-dioxolane-4-methanamine (105281-24-1,105369-31-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) THF, 0 deg C, 30 min, 2.) THF, RT, 2 h

2: 85 percent / DIBAL / toluene / 0.5 h

3: 1.) NaH / 1.) Et₂O, RT, 15 min, 2.) Et₂O, from -15 deg C to RT, 30 min

4: xylene / 48 h / Heating

5: 82 percent / 1 N aq. KOH / tetrahydrofuran / 4 h / 60 °C

With potassium hydroxide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; toluene; xylene;

DOI:10.1021/jo00375a057

upstream raw materials:

N-<1-<<4S-<4α,4(S^*),5β>>-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenyl>-2,2,2-trichloroacetamide

(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

(E)-ethyl 3-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acrylate

(E)-3-<(4S-trans)-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenol

Downstream raw materials:

1,1-dimethylethyl N-<1-<<4S-<4α,4(S^*),5β>>-<2,2-dimethyl>-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenyl>carbamate

N-<1-<<4S-<4α,4,(S^*),5β>>-2,2-dimethyl-5-<(phenylmethoxy)methyl>-1,3-dioxolan-4-yl>-2-propenyl>-4-chlorobenzamide

(R)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-propylamine

((1R,2S,3S)-4-Benzyloxy-1-ethyl-2,3-dihydroxy-butyl)-carbamic acid benzyl ester

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