(E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol

Base Information

• Chemical Name: (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol
• CAS No.: 1197190-14-9
• Molecular Formula: C₂₁H₃₂O₆
• Molecular Weight: 380.481

Synonyms:(E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol

Chemical Property of (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol

Chemical Property:

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Technology Process of (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol

There total 2 articles about (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol 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: 79.0%

(E,4R,5R)-7-(4-methoxybenzyloxy)-4-hydroxy-5-(methoxymethoxy)-4-methylhept-2-enal (1197190-12-7) + allylmagnesium bromide (1730-25-2) → (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol (1197190-14-9)

Guidance literature:

allylmagnesium bromide; With (+)-β-methoxydiisopinocampheylborane; In diethyl ether; at -78 - 20 ℃;

(E,4R,5R)-7-(4-methoxybenzyloxy)-4-hydroxy-5-(methoxymethoxy)-4-methylhept-2-enal; In diethyl ether; at -78 ℃; for 1h;

With dihydrogen peroxide; sodium hydroxide; In water; at 0 - 20 ℃;

DOI:10.1039/b912267b

Reference yield:

(E,4R,5R)-7-(4-methoxybenzyloxy)-4-hydroxy-5-(methoxymethoxy)-4-methylhept-2-enal (1197190-12-7) + allyltrimethoxysilane (2551-83-9) → (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol (1197190-14-9) + (E,4S,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol

Guidance literature:

With methanol; silver fluoride; (R)-tol-BINAP; at -20 ℃; for 5h; optical yield given as %de;

DOI:10.1039/b912267b

Reference yield: 78.0%

(E,4R,7R,8R)-10-(4-methoxybenzyloxy)-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4,7-diol (1197190-14-9) + acryloyl chloride (814-68-6,25189-84-8) → (E,4R,7R,8R)-10-(4-methoxybenzyloxy)-7-hydroxy-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4-yl acrylate (1197190-16-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1039/b912267b

upstream raw materials:

(E,4R,5R)-7-(4-methoxybenzyloxy)-4-hydroxy-5-(methoxymethoxy)-4-methylhept-2-enal

allyltrimethoxysilane

allylmagnesium bromide

Downstream raw materials:

(E,4R,7R,8R)-10-(4-methoxybenzyloxy)-7-hydroxy-8-(methoxymethoxy)-7-methyldeca-1,5-diene-4-yl acrylate

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