2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester

Base Information

• Chemical Name: 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester
• CAS No.: 934686-96-1
• Molecular Formula: C₄₇H₆₇NO₁₄
• Molecular Weight: 870.047

Synonyms:2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester

Chemical Property of 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester

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Technology Process of 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) ester

There total 4 articles about 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl) 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: 85.0%

5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11(12)-taxadiene (119777-85-4) + (4S,5R)-N-(tert-butoxycarbonyl)-2-(2,4-dimethoxyphenyl)-4-iso-butyl-5-oxazolidinecarboxylic acid (191276-34-3) → 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (934686-96-1)

Guidance literature:

With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In toluene;

DOI:10.1016/j.bmcl.2006.12.101

Reference yield:

acetic acid 7,10,13-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0(3,8)]pentadec-11-en-9-ylester (87193-98-4) → 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (934686-96-1)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. LiOH / methanol / 4 °C

2: 85 percent / EDC; DMAP / toluene

With dmap; lithium hydroxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; toluene;

DOI:10.1016/j.bmcl.2006.12.101

Reference yield:

2-desacetoxytaxinine J (119347-14-7) → 2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-(7,9,10-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.03,8]pentadec-11-en-13-yl) ester (934686-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1: NH₂OH*HCl; aq. NaOAc / ethanol / Heating

2: aq. LiOH / methanol / 4 °C

3: 85 percent / EDC; DMAP / toluene

With dmap; lithium hydroxide; hydroxylamine hydrochloride; sodium acetate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In methanol; ethanol; toluene;

DOI:10.1016/j.bmcl.2006.12.101

upstream raw materials:

5α,13α-dihydroxy-7β,9α,10β-triacetoxy-4(20),11(12)-taxadiene

(4S,5R)-N-(tert-butoxycarbonyl)-2-(2,4-dimethoxyphenyl)-4-iso-butyl-5-oxazolidinecarboxylic acid

acetic acid 7,10,13-triacetoxy-5-hydroxy-8,12,15,15-tetramethyl-4-methylene-tricyclo[9.3.1.0(3,8)]pentadec-11-en-9-ylester

2-desacetoxytaxinine J

Downstream raw materials:

2-(2,4-dimethoxy-phenyl)-4-isobutyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-[7,9,10-triacetoxy-8,12,15,15-tetramethyl-4-methylene-5-(3-phenyl-acryloyloxy)-tricyclo[9.3.1.0^3,8]pentadec-11-en-13-yl] ester

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