(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

Base Information

Chemical Name:(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al
CAS No.:236401-72-2
Molecular Formula:C₂₂H₃₄O₅
Molecular Weight:378.509
Hs Code.:

Synonyms:(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

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Chemical Property of (2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

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Technology Process of (2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

There total 10 articles about (2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al 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: 96.0%

: 236401-70-0
(2S,3S,4R,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-ol

: 236401-72-2
(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - -20 ℃; for 1.5h;
DOI:10.1021/ol990004c

Reference yield:

: 236401-60-8
(2S,4R,5R)-5-hydroxy-4-methyl-3-oxohexan-2-yl benzoate

: 236401-72-2
(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / triflic acid / diethyl ether / 4 h / 20 °C

2.1: NaBH₄ / methanol / 0.5 h / 20 °C

3.1: 8.02 g / K₂CO₃ / methanol / 4 h / 20 °C

4.1: 96 percent / NaIO₄ / methanol; H₂O / 1 h / 20 °C

5.1: dicyclohexylboron chloride; Et₃N / diethyl ether / 2 h / -10 - 0 °C

5.2: diethyl ether / 19 h / -78 - -20 °C

5.3: 96 percent / aq. H₂O₂ / methanol; various solvent(s) / 2 h / 0 °C / pH 7

6.1: 99 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 16.5 h / -30 - -20 °C

7.1: 93 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

8.1: 96 percent / H₂ / W-2 Raney nickel / ethanol / 16 h / 20 °C

9.1: 96 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 - -20 °C

With sodium tetrahydroborate; sodium periodate; oxalyl dichloride; trifluorormethanesulfonic acid; dicyclohexylboron chloride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; tetramethylammonium triacetoxyborohydride; W-2 Raney nickel; In methanol; diethyl ether; ethanol; dichloromethane; water; acetic acid; acetonitrile; 9.1: Swern oxidation;
DOI:10.1021/ol990004c

Reference yield:

: 236401-77-7
(2S,3S,4R,5R,6S,7R)-1-benzyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-octandiol

: 236401-72-2
(2R,3R,4S,5S,6R,7R)-7-(4-methoxybenzyloxy)-3,5-isopropylidenedioxy-2,4,6-trimethyloctan-1-al

Guidance literature:: Multi-step reaction with 3 steps

1: 93 percent / PPTS / CH₂Cl₂ / 24 h / 20 °C

2: 96 percent / H₂ / W-2 Raney nickel / ethanol / 16 h / 20 °C

3: 96 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 - -20 °C

With oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; W-2 Raney nickel; In ethanol; dichloromethane; 3: Swern oxidation;
DOI:10.1021/ol990004c