(R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 143674-56-0
• Molecular Formula: C₃₃H₄₁NO₇
• Molecular Weight: 563.691

Synonyms:(R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 13 articles about (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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: 80.0%

benzyl bromide (100-39-0) + (R)-4-(6'-Hydroxymethyl-6,2',4'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester → (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (143674-56-0)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 20h; Ambient temperature;

DOI:10.1016/0040-4039(92)88096-N

Reference yield:

3,5-dimethoxybenzyl alcohol (705-76-0) → (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (143674-56-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / NBS / CHCl₃ / 45 °C

2: 90 percent / PDC / CHCl₃

3: 85 percent / NaClO₂ / dimethylsulfoxide / 12 h / Ambient temperature

4: SOCl₂ / Heating

5: Et₃N, DMAP / CHCl₃ / 0 °C

6: 25 percent / NaOAc / Pd(PPh₃)2Cl₂ / N,N-dimethyl-acetamide / 130 °C

7: 68 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

8: 90 percent / K₂CO₃ / acetone / 3 h / Ambient temperature

9: 80 percent / NaH / tetrahydrofuran / 20 h / Ambient temperature

With dmap; sodium chlorite; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; sodium acetate; sodium hydride; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide; acetone;

DOI:10.1016/0040-4039(92)88096-N

Reference yield:

methyl 3,5-dimethoxybenzoate (2150-37-0) → (R)-4-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (143674-56-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 92 percent / LiAlH₄ / tetrahydrofuran / 10 h / Ambient temperature

2: 96 percent / NBS / CHCl₃ / 45 °C

3: 90 percent / PDC / CHCl₃

4: 85 percent / NaClO₂ / dimethylsulfoxide / 12 h / Ambient temperature

5: SOCl₂ / Heating

6: Et₃N, DMAP / CHCl₃ / 0 °C

7: 25 percent / NaOAc / Pd(PPh₃)2Cl₂ / N,N-dimethyl-acetamide / 130 °C

8: 68 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

9: 90 percent / K₂CO₃ / acetone / 3 h / Ambient temperature

10: 80 percent / NaH / tetrahydrofuran / 20 h / Ambient temperature

With dmap; sodium chlorite; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; thionyl chloride; sodium acetate; sodium hydride; potassium carbonate; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; chloroform; N,N-dimethyl acetamide; dimethyl sulfoxide; acetone;

DOI:10.1016/0040-4039(92)88096-N

upstream raw materials:

benzyl bromide

3,5-dimethoxybenzyl alcohol

2-Brom-3.5-dimethoxy-benzoylchlorid

methyl 3,5-dimethoxybenzoate

Downstream raw materials:

(S)-[5'-((R)-Acetylamino-methoxycarbonyl-methyl)-4,6,2'-trimethoxy-biphenyl-2-yl]-((R)-2-hydroxy-1-phenyl-ethylamino)-acetic acid methyl ester

(R)-Acetylamino-(2'-benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-acetic acid methyl ester

N-[(R)-1-(2'-Benzyloxymethyl-6,4',6'-trimethoxy-biphenyl-3-yl)-2-hydroxy-ethyl]-acetamide

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