2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

Base Information

• Chemical Name: 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate
• CAS No.: 1141365-47-0
• Molecular Formula: C₄₅H₅₈O₇Si
• Molecular Weight: 739.037
• Mol file: 1141365-47-0.mol

Synonyms:2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

Chemical Property of 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate

There total 47 articles about 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate 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: 78.0%

C39H50O7Si (1182098-75-4) + allyl bromide (106-95-6) → 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-47-0)

Guidance literature:

With potassium carbonate; Inert atmosphere;

DOI:10.1021/ol102652t

Reference yield: 32.0%

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde (1141365-72-1) + allyl bromide (106-95-6) + 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid (186774-95-8) → 2-propenyl (2S,3S,3'aS,4S,5'R)-3',3'a,4,5,5',6'-hexahydro-4-[2-hydroxyethyl]-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-48-1) + 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-47-0)

Guidance literature:

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde; 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid; In methanol; at 25 ℃; for 60h;

allyl bromide; With potassium carbonate; In N,N-dimethyl-formamide; at 25 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.200805488

Reference yield:

(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone (1141365-67-4) → 2-propenyl (2S,3S,3'aS,4S,5'R)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3',3'a,4,5,5',6'-hexahydro-3-methyl-5'-pentyl-8'-(2-propenyloxy)-spiro[furan-2(3H),2'-[2H]pyrano[2,3,4-de][1]benzopyran]-9'-carboxylate (1141365-47-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: toluene / 24 h / 65 °C / Inert atmosphere

2.1: tert-butylmagnesium chloride / 3 h / -78 - 20 °C / Inert atmosphere

2.2: 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 60 h / 60 °C / Inert atmosphere

4.1: CeCl₃*LiCl / tetrahydrofuran; diethyl ether / 0.75 h / 0 °C / Inert atmosphere

4.2: 0.75 h / -78 °C / Inert atmosphere

4.3: 0.25 h / -78 °C / Inert atmosphere

5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.08 h / -110 °C / Inert atmosphere

5.2: 1 h / -110 - 0 °C / Inert atmosphere

6.1: 10% palladium on activated charcoal; hydrogen / ethyl acetate / 4 h

7.1: potassium carbonate / Inert atmosphere

With 10% palladium on activated charcoal; CeCl₃*LiCl; tert-butylmagnesium chloride; hydrogen; tert.-butyl lithium; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; chloroform; ethyl acetate; toluene; pentane;

DOI:10.1021/ol102652t

upstream raw materials:

(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde

allyl bromide

2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid

(3S,4S)-dihydro-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]-3-methyl-2(3H)-furanone