propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester

Base Information

• Chemical Name: propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester
• CAS No.: 627101-58-0
• Molecular Formula: C₃₄H₅₅IO₇Si
• Molecular Weight: 730.797
• Mol file: 627101-58-0.mol

Synonyms:propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester

Chemical Property of propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester

There total 11 articles about propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl 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:

propionaldehyde (123-38-6) + (6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one (627101-48-8) → propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester (627101-58-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -20 ℃;

DOI:10.1021/ol0357853

Reference yield:

(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane (76927-59-8) → propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester (627101-58-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 52 percent / titanium tetraisopropoxide; (R)-BINOL; molecular sieves 4 Angstroem / tetrahydrofuran / 14 h / -20 °C

2.1: imidazole / CH₂Cl₂

3.1: DIBAL / CH₂Cl₂ / -78 °C

4.1: MnO₂ / CH₂Cl₂

5.1: c-Hex₂BCl; Et₃N / diethyl ether / -20 °C

5.2: diethyl ether / -78 - -30 °C

6.1: SmI₂ / tetrahydrofuran / -20 °C

With 1H-imidazole; titanium(IV) isopropylate; manganese(IV) oxide; samarium diiodide; 4 A molecular sieve; dicyclohexylboron chloride; (R)-1,1'-Bi-2-naphthol; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Mukaiyama aldol reaction;

DOI:10.1021/ol0357853

Reference yield:

(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate (905589-59-5) → propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1S,2R,3S)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-hydroxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester (627101-58-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: PPTS / CH₂Cl₂

2.1: i-PrMgCl / tetrahydrofuran / -20 °C

3.1: tetrahydrofuran / 0 °C

4.1: c-Hex₂BCl; Et₃N / diethyl ether / -20 °C

4.2: diethyl ether / -78 - -30 °C

5.1: SmI₂ / tetrahydrofuran / -20 °C

With samarium diiodide; dicyclohexylboron chloride; isopropylmagnesium chloride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ol0357853

upstream raw materials:

propionaldehyde

(6E,10E,12E)(2R,4R,5R,13R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-5-hydroxy-13-iodo-2,4,7-trimethyl-trideca-6,10,12-trien-3-one

(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

(3,4-dimethoxoxyphenyl)methyl 2,2,2-trichloroacetimidate

Downstream raw materials:

propionic acid (1R,5R)-5-(tert-butyldimethyl-silanyloxy)-1-[(1R,2R,3R)-4-(3,4-dimethoxy-benzyloxy)-1,3-dimethyl-2-triethylsilanyloxy-butyl]-(2E,6E,8E)-9-iodo-3-methyl-nona-2,6,8-trienyl ester

(6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-trien-5-ol

(6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene