(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

Base Information

Chemical Name:(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol
CAS No.:1268161-83-6
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

Synonyms:(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

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Chemical Property of (3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

Chemical Property:

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Technology Process of (3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

There total 5 articles about (3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-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:

: 250379-06-7
(2R,3R)-5-(4-methoxybenzyloxy)-2-methyl-3-(triethylsilyloxy)-pentanal

: 1826-67-1
vinyl magnesium bromide

: 1268161-83-6
(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

: 1268161-84-7
(3S,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

Guidance literature:: (2R,3R)-5-(4-methoxybenzyloxy)-2-methyl-3-(triethylsilyloxy)-pentanal; vinyl magnesium bromide; In tetrahydrofuran; at -78 ℃; for 1.5h;

With ammonium chloride; In tetrahydrofuran; water; at -78 - 20 ℃; optical yield given as %de; diastereoselective reaction;
DOI:10.1002/anie.201005226

Reference yield:

: 1268161-79-0
3-(R)-hydroxy-5-(4-methoxy-benzyloxy)-2-(R)-methyl-pentanoic acid 2-[benzyl-(2,4,6-trimethylbenzolsulfonyl)-amino]-1-phenyl-propyl ester

: 1268161-83-6
(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,6-dimethylpyridine / dichloromethane / 1.17 h / -78 °C

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 6 h / -78 - -50 °C

2.2: 20 °C

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

4.1: tetrahydrofuran / 1.5 h / -78 °C

4.2: -78 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1002/anie.201005226

Reference yield:

: 1268161-82-5
(2S,3R)-5-(4-methoxybenzyloxy)-2-methyl-3-(triethylsilyloxy)-pentane-1-ol

: 1268161-83-6
(3R,4S,5R)-7-(4-methoxybenzyloxy)-4-methyl-5-(triethylsilyloxy)-hept-1-ene-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 20 °C

2.1: tetrahydrofuran / 1.5 h / -78 °C

2.2: -78 - 20 °C

With sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1002/anie.201005226