2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester

Base Information

• Chemical Name: 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester
• CAS No.: 646030-62-8
• Molecular Formula: C₄₄H₆₆O₇Si
• Molecular Weight: 735.089
• Mol file: 646030-62-8.mol

Synonyms:2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester

Chemical Property of 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester

There total 19 articles about 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-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:

3-oxohexanoic acid tert-butyl ester (61540-30-5) → 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester (646030-62-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 83 percent / H₂ / [((R)-Binap)-RuCl₂]2(NEt₃) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr

2.1: 87 percent / DMAP; EDCl / CH₂Cl₂ / 16 h / 20 °C

3.1: 100 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

4.1: 100 percent / (COCl)2; DMF / CH₂Cl₂

5.1: Zn-Cu; DMA; TMSCl / toluene / 50 °C

5.2: 84 mg / Pd₂(dba)3; P(furyl)3 / toluene

With triethylsilane; dmap; chloro-trimethyl-silane; oxalyl dichloride; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; trifluoroacetic acid; zinc; [((R)-Binap)-RuCl₂]2; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1021/ja038216z

Reference yield:

ethyl butyroyl acetate (3249-68-1) → 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester (646030-62-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 59 percent / t-BuOK / benzene / 144 h / Heating

2.1: 83 percent / H₂ / [((R)-Binap)-RuCl₂]2(NEt₃) / tetrahydrofuran; methanol / 17 h / 90 - 95 °C / 7500.6 Torr

3.1: 87 percent / DMAP; EDCl / CH₂Cl₂ / 16 h / 20 °C

4.1: 100 percent / Et₃SiH; trifluoroacetic acid / CH₂Cl₂ / 1.5 h / 20 °C

5.1: 100 percent / (COCl)2; DMF / CH₂Cl₂

6.1: Zn-Cu; DMA; TMSCl / toluene / 50 °C

6.2: 84 mg / Pd₂(dba)3; P(furyl)3 / toluene

With triethylsilane; dmap; chloro-trimethyl-silane; oxalyl dichloride; potassium tert-butylate; hydrogen; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; trifluoroacetic acid; zinc; [((R)-Binap)-RuCl₂]2; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1021/ja038216z

Reference yield:

(S)-2-Methyl-pent-4-enoic acid (R)-1-chlorocarbonylmethyl-butyl ester (501015-63-0) + (2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane (646030-61-7) → [(1R,2S)-1-((2R,4S,5S)-5-Allyl-4-methyl-tetrahydro-furan-2-ylmethyl)-2-methoxymethoxy-3-methyl-butoxy]-tert-butyl-diphenyl-silane + 2-methylpent-4-enoic acid [(2R,3S,1'R,4'S,5'S)-(-)-[1-(2-tert-butyldiphenylsilyloxy-3-methoxymethoxy-3-isopropylprop-1-yl)-5-methyl-7-oxanorborn-2-yl]-2-one]hept-4-yl ester + 2-methylpent-4-enoic acid [(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-6-one]undec-8-yl ester (646030-62-8)

Guidance literature:

(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane; With chloro-trimethyl-silane; 2,4-dichlorophenoxyacetic acid dimethylamine; copper; zinc; In toluene; at 50 ℃;

(S)-2-Methyl-pent-4-enoic acid (R)-1-chlorocarbonylmethyl-butyl ester; With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; P(furyl)3; In toluene;

DOI:10.1021/ja038216z

upstream raw materials:

(S)-2-Methyl-pent-4-enoic acid (R)-1-chlorocarbonylmethyl-butyl ester

(2R,3S,4R,2'R,4'S,5'S)-(-)-1-(5-allyl-4-methyltetrahydrofuran-2-yl)-2-(tert-butyldiphenylsilanyloxy)-3-methoxymethoxy-4-methyl-5-iodopentane

(S)-2-methyl-4-pentenoic acid

3-oxohexanoic acid tert-butyl ester

Downstream raw materials:

(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-methoxymethoxy-6,13,19-trimethyl-9-propyl-8,20-dioxabicyclo[15.2.1]eicosane-7,11-dione

(1S,6S,9R,13R,14S,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-14-hydroxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosan-7-one

(1S,6S,9R,13R,15R,17R,19S)-(-)-15-tert-butyldiphenylsilyloxy-6,13,19-trimethyl-11-methylene-9-propyl-8,20-dioxabicyclo[15.2.1]eicosane-7,14-dione