(3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one
• CAS No.: 144068-37-1
• Molecular Formula: C₃₂H₅₁IO₅Si
• Molecular Weight: 670.744
• Mol file: 144068-37-1.mol

Synonyms:

Chemical Property of (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one

There total 4 articles about (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one 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:

(E)-(R)-6-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-2-(4-methoxy-benzyloxy)-2-methyl-hept-4-enoic acid (144068-36-0,144125-17-7) → (3R,5R)-5-{(1S,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one (144125-15-5) + (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one (144068-37-1)

Guidance literature:

With 2,4,6-trimethyl-pyridine; iodine; In acetonitrile; at -30 ℃; Yield given. Yields of byproduct given;

DOI:10.1039/c39920001229

Reference yield:

[1R-[1β,[αS*,βS*],3aα,4aβ,7aβ]]-octahydro-β,7a-dimethyl-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-α-ethenyl-1H-indene-1-ethanol (93489-72-6) → (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one (144068-37-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (morpho CDI), 4 A molecular sieves / CH₂Cl₂

2: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT

3: Ambient temperature

4: I₂, 2,4,6-collidine / acetonitrile / -30 °C

With 2,4,6-trimethyl-pyridine; 4 A molecular sieve; iodine; N-cyclohexyl-N'-β-(4-methylmorpholinium)ethylcarbodiimide p-toluenesulfonate; lithium diisopropyl amide; In dichloromethane; acetonitrile;

DOI:10.1039/c39920001229

Reference yield:

2-(4-Methoxy-benzyloxy)-propionic acid (S)-1-{(S)-1-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-ethyl}-allyl ester (144068-34-8) → (3R,5S)-5-{(1R,2S)-2-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-1-iodo-propyl}-3-(4-methoxy-benzyloxy)-3-methyl-dihydro-furan-2-one (144068-37-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, -78 deg C, 2.) THF, from -78 deg C to RT

2: Ambient temperature

3: I₂, 2,4,6-collidine / acetonitrile / -30 °C

With 2,4,6-trimethyl-pyridine; iodine; lithium diisopropyl amide; In acetonitrile;

DOI:10.1039/c39920001229

upstream raw materials:

(E)-(R)-6-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-2-(4-methoxy-benzyloxy)-2-methyl-hept-4-enoic acid

[1R-[1β,[αS*,βS*],3aα,4aβ,7aβ]]-octahydro-β,7a-dimethyl-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-α-ethenyl-1H-indene-1-ethanol

2-(4-Methoxy-benzyloxy)-propionic acid (S)-1-{(S)-1-[(1R,3aR,4S,7aR)-4-(tert-butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-ethyl}-allyl ester

Downstream raw materials:

(E)-(R)-6-[(1R,3aR,4S,7aR)-4-(tert-Butyl-dimethyl-silanyloxy)-7a-methyl-octahydro-inden-1-yl]-2-(4-methoxy-benzyloxy)-2-methyl-hept-4-enoic acid