(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate

Base Information

• Chemical Name: (4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate
• CAS No.: 1298015-31-2
• Molecular Formula: C₂₁H₃₁O₈P
• Molecular Weight: 442.446
• Mol file: 1298015-31-2.mol

Synonyms:(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate

Chemical Property of (4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate

There total 1 articles about (4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate 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: 83.0%

cis-1,4-bis(acetyloxy)but-2-ene (25260-60-0) + (4R,6S)-4-((S)-but-3-en-2-yl)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)ethyl)-1,3,2-dioxaphosphinane 2-oxide (1298015-30-1) → (4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate (1298015-31-2)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 45 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo200337v

Reference yield: 94.0%

(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate (1298015-31-2) → (4S,6R)-2-methoxy-4-(2-((4-methoxybenzyl)oxy)ethyl)-6-((S)-pent-4-en-2-yl)-1,3,2-dioxaphosphinane 2-oxide (1298015-32-3)

Guidance literature:

With ammonium formate; palladium diacetate; triphenylphosphine; In 1,2-dichloro-ethane; at 90 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo200337v

Reference yield:

(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate (1298015-31-2) → (5R,7S)-9,9-diisopropyl-7-(2-((4-methoxybenzyl)oxy)ethyl)-10-methyl-5-((S)-pent-4-en-2-yl)-2,4,8-trioxa-9-silaundecane (1298015-34-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonium formate; palladium diacetate; triphenylphosphine / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

2: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; ammonium formate; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo200337v

upstream raw materials:

cis-1,4-bis(acetyloxy)but-2-ene

(4R,6S)-4-((S)-but-3-en-2-yl)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)ethyl)-1,3,2-dioxaphosphinane 2-oxide

Downstream raw materials:

(4S,6R)-2-methoxy-4-(2-((4-methoxybenzyl)oxy)ethyl)-6-((S)-pent-4-en-2-yl)-1,3,2-dioxaphosphinane 2-oxide

(3S,5R,6S)-1-((4-methoxybenzyl)oxy)-6-methylnon-8-ene-3,5-diol

(4S,5R,7S)-9-((4-methoxybenzyl)oxy)-4-methyl-7-((triisopropylsilyl)oxy)non-1-en-5-ol

(5R,7S)-9,9-diisopropyl-7-(2-((4-methoxybenzyl)oxy)ethyl)-10-methyl-5-((S)-pent-4-en-2-yl)-2,4,8-trioxa-9-silaundecane