(2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal
• CAS No.: 156629-02-6
• Molecular Formula: C₁₉H₂₈O₅
• Molecular Weight: 336.428
• Mol file: 156629-02-6.mol

Synonyms:(2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal

Chemical Property of (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal

There total 9 articles about (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal 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)-1-benzyloxy-2-methylpentan-3-one (116546-78-2) → (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal (156629-02-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) (cyclohexyl)2BCl, Et₃N, 3.) 30percent aq. H₂O₂, pH 7 buffer

2: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

3: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

4: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 30 min

6: CH₂Cl₂; tetrahydrofuran / 0.25 h / -100 °C

7: 1.) KH / 1.) THF, 5 min, 2.) THF, from 0 to 20 deg C, 1.5 h

8: 1.) aq. OsO₄, N-methylmorpholine N-oxide, 2.) NaIO₄, pH 7 buffer / 1.) t-BuOH, THF, 20 deg C, 15 h, 2.) t-BuOH, THF, 20 deg C, 25 min

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; lithium 4,4′-di(tert-butyl)biphenyl; pH 7 buffer; dicyclohexylboron chloride; dihydrogen peroxide; potassium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00104a010

Reference yield:

(2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol (128146-35-0,128241-48-5) → (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal (156629-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

2: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 30 min

4: CH₂Cl₂; tetrahydrofuran / 0.25 h / -100 °C

5: 1.) KH / 1.) THF, 5 min, 2.) THF, from 0 to 20 deg C, 1.5 h

6: 1.) aq. OsO₄, N-methylmorpholine N-oxide, 2.) NaIO₄, pH 7 buffer / 1.) t-BuOH, THF, 20 deg C, 15 h, 2.) t-BuOH, THF, 20 deg C, 25 min

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; lithium 4,4′-di(tert-butyl)biphenyl; pH 7 buffer; potassium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00104a010

Reference yield:

(2S,4S,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one (116546-79-3,116661-38-2,128241-46-3,141611-63-4) → (2R,3R,4S,5S,6R)-2,4-(S)-(ethylidenedioxy)-6-<(p-methoxybenzyl)oxy>-3,5-dimethylheptanal (156629-02-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / Me₄NHB(OAc)3, AcOH / acetonitrile / 50.5 h / -30 - -20 °C

2: 93 percent / p-TsOH / CH₂Cl₂ / 70 h

3: 97 percent / LiDBB / tetrahydrofuran / 0.5 h / -78 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, from -78 to -23 deg C, 30 min

5: CH₂Cl₂; tetrahydrofuran / 0.25 h / -100 °C

6: 1.) KH / 1.) THF, 5 min, 2.) THF, from 0 to 20 deg C, 1.5 h

7: 1.) aq. OsO₄, N-methylmorpholine N-oxide, 2.) NaIO₄, pH 7 buffer / 1.) t-BuOH, THF, 20 deg C, 15 h, 2.) t-BuOH, THF, 20 deg C, 25 min

With sodium periodate; osmium(VIII) oxide; oxalyl dichloride; lithium 4,4′-di(tert-butyl)biphenyl; pH 7 buffer; potassium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ja00104a010

upstream raw materials:

(S)-1-benzyloxy-2-methylpentan-3-one

(2S,3S,4S,5S,6E)-1-(benzyloxy)-2,4-dimethyl-6-octene-3,5-diol

(2S,4S,5S,6E)-1-(benzyloxy)-5-hydroxy-2,4-dimethyl-6-octen-3-one

(2S,3S,4S,5S,6E)-3,5-(R)-(ethylidenedioxy)-2,4-dimethyl-6-octen-1-ol

Downstream raw materials:

(R)-2-Benzenesulfinyl-3-[(4R,5S,6R)-6-((S)-2-benzyloxy-1-methyl-ethyl)-2,2,5-trimethyl-[1,3]dioxan-4-yl]-1-{(2S,4R,5R,6S)-6-[(1S,2R)-2-(4-methoxy-benzyloxy)-1-methyl-propyl]-2,5-dimethyl-[1,3]dioxan-4-yl}-butan-1-ol

(2R,3S,4R,5S,6S,8S,9R,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-9,11-dihydroxy-2,4,6,10,12,13-hexamethyltetradecanolide

(2R,3S,4R,5S,6S,8S,10R,11R,12R,13R)-3,5-<(p-bromobenzylidene)dioxy>-8,8-(epoxymethano)-11-hydroxy-2,4,6,10,12,13-hexamethyl-9-oxotetradecanolide