(E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one

Base Information

• Chemical Name: (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one
• CAS No.: 332179-77-8
• Molecular Formula: C₂₇H₄₅IO₄Si
• Molecular Weight: 588.642
• Mol file: 332179-77-8.mol

Synonyms:(E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one

Chemical Property of (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one

There total 8 articles about (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-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: 80.0%

p-methoxybenzyl trichloroacetate (56599-24-7) + (E)-(4S,6R,7S)-4-Hydroxy-9-iodo-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one (332179-85-8) → (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one (332179-77-8)

Guidance literature:

With trifluorormethanesulfonic acid; In diethyl ether; at 0 ℃; for 3h;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

(E)-(3R,4S)-6-Iodo-4-methyl-3-triisopropylsilanyloxy-hex-5-enal (332179-82-5) → (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one (332179-77-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / 0.58 h / 0 °C

1.2: diethyl ether / 1 h / -78 °C

1.3: H₂O₂ / methanol / pH 7

2.1: 80 percent / TfOH / diethyl ether / 3 h / 0 °C

With trifluorormethanesulfonic acid; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether;

DOI:10.1016/S0040-4039(00)02205-X

Reference yield:

(E)-(3R,4S)-6-Iodo-4-methyl-3-triisopropylsilanyloxy-hex-5-en-1-ol → (E)-(4S,6R,7S)-9-Iodo-4-(4-methoxy-benzyloxy)-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one (332179-77-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Dess-Martin periodinane / CH₂Cl₂

2.1: (-)-Ipc₂BCl; Et₃N / diethyl ether / 0.58 h / 0 °C

2.2: diethyl ether / 1 h / -78 °C

2.3: H₂O₂ / methanol / pH 7

3.1: 80 percent / TfOH / diethyl ether / 3 h / 0 °C

With trifluorormethanesulfonic acid; Dess-Martin periodane; triethylamine; (-)-diisopinocamphenylborane chloride; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)02205-X

upstream raw materials:

p-methoxybenzyl trichloroacetate

(E)-(4S,6R,7S)-4-Hydroxy-9-iodo-7-methyl-6-triisopropylsilanyloxy-non-8-en-2-one

(E)-(3R,4S)-6-Iodo-4-methyl-3-triisopropylsilanyloxy-hex-5-enal

(2R,3R)-5-Benzyloxy-2-methyl-3-triisopropylsilanyloxy-pentanal

Downstream raw materials:

(E)-(2S,4S,8S,10R,11S)-1-{(4R,6R)-6-[(E)-(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-hex-1-enyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-4-hydroxy-13-iodo-2,8-bis-(4-methoxy-benzyloxy)-11-methyl-10-triisopropylsilanyloxy-tridec-12-en-6-one