(2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol

Base Information

• Chemical Name: (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol
• CAS No.: 1158302-78-3
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498
• Mol file: 1158302-78-3.mol

Synonyms:(2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol

Chemical Property of (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol

There total 2 articles about (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol 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: 92.0%

(2R,3R,4S,5R,6R)-5-[(4-methoxybenzyl)oxy]-2,4,6-trimethylheptane-1,3,7-triol (1158302-56-7) + 2,2-dimethoxy-propane (77-76-9) → (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol (1158302-78-3)

Guidance literature:

With camphor-10-sulfonic acid; In diethyl ether; dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2008.12.049

Reference yield:

C18H24O5 → (2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol (1158302-78-3)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C

2: camphor-10-sulfonic acid / dichloromethane / 1 h / 0 - 20 °C

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetlet.2018.06.020

Reference yield: 95.0%

(2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol (1158302-78-3) + benzyl bromide (100-39-0) → (4R,5R)-4-{(1R,2R,3R)-4-(benzyloxy)-2-[(4-methoxybenzyl)oxy]-1,3-dimethylbutyl}-2,2,5-trimethy-1,3-dioxane (1158302-57-8)

Guidance literature:

(2R,3R,4R)-3-(4-methoxybenzyloxy)-2-methyl-4-[2,2,5-trimethyl-(4S,5S)-1,3-dioxan-4-yl]pentan-1-ol; With sodium hydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere; Reflux;

benzyl bromide; In tetrahydrofuran; for 3h; Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2008.12.049

upstream raw materials:

(2R,3R,4S,5R,6R)-5-[(4-methoxybenzyl)oxy]-2,4,6-trimethylheptane-1,3,7-triol

2,2-dimethoxy-propane

Downstream raw materials:

(4R,5R)-4-{(1R,2R,3R)-4-(benzyloxy)-2-[(4-methoxybenzyl)oxy]-1,3-dimethylbutyl}-2,2,5-trimethy-1,3-dioxane