(2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane

Base Information

• Chemical Name: (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane
• CAS No.: 217939-77-0
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 217939-77-0.mol

Synonyms:(2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane

Chemical Property of (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane

There total 2 articles about (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane 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:

(S)-2-[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-butan-1-ol → (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane (217939-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO; 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 1 h; 2.) -60 deg C to r.t.

2: n-BuLi / tetrahydrofuran / 12 h / Ambient temperature

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)01825-5

Reference yield:

Methyltriphenylphosphonium bromide (1779-49-3) + (S)-2-[(2R,4S,5R)-4-Allyl-2-(4-methoxy-phenyl)-[1,3]dioxan-5-yloxy]-butyraldehyde → (2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane (217939-77-0)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; for 12h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(98)01825-5

Reference yield: 94.0%

(2R,4S,5R)-4-Allyl-5-((S)-1-ethyl-allyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxane (217939-77-0) → (2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene (217939-79-2)

Guidance literature:

Grubbs catalyst first generation; In benzene; for 12h; Ambient temperature;

DOI:10.1016/S0040-4039(98)01825-5

upstream raw materials:

Methyltriphenylphosphonium bromide

Downstream raw materials:

(2R,4aR,6S,9aS)-6-Ethyl-2-(4-methoxy-phenyl)-4a,6,9,9a-tetrahydro-4H-1,3,5-trioxa-benzocycloheptene

(1aR,2aS,4R,6aR,8S,8aR)-8-Ethyl-4-(4-methoxy-phenyl)-hexahydro-1,3,5,7-tetraoxa-benzo[a]cyclopropa[d]cycloheptene