(2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal

Base Information

• Chemical Name: (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal
• CAS No.: 124871-71-2
• Molecular Formula: C₂₅H₄₀O₇
• Molecular Weight: 452.588
• Mol file: 124871-71-2.mol

Synonyms:

Chemical Property of (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal

There total 19 articles about (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal 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:

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane (87641-44-9,98049-27-5) → (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal (124871-71-2)

Guidance literature:

Multi-step reaction with 17 steps

1: pyridine / CH₂Cl₂ / 0 deg C, rt, 10.5 h

2: CSA / CH₂Cl₂ / 2 h / Ambient temperature

3: 1N KOH / methanol / 18 h / Ambient temperature

4: 94 percent / oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -60 - -50 °C

5: 99 percent / LDA / tetrahydrofuran / -83 deg C, -20 deg C, 2 h

6: 90 percent / Et₃N / benzene / 0.33 h / 7 °C

7: 99 percent / NaOEt / tetrahydrofuran / 3.5 h / Ambient temperature

8: 78 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

9: m-CPBA / CH₂Cl₂ / 2.5 h / -20 °C

10: 1M n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

11: 46 percent / H₂ / 5percent Pt-C / benzene / 1 h / 8 - 10 °C

12: 84 percent / pyridine / CH₂Cl₂ / 35 h / Ambient temperature

13: 76 percent / 4N HCl / tetrahydrofuran / 13 h / Ambient temperature

14: 91 percent / PPTS / CH₂Cl₂ / 0.42 h / Ambient temperature

15: diisopropylethylamine / CH₂Cl₂ / RT, 45/50 deg C, 12 h

16: 1N NaOH / dioxane / 14 h / 65 - 70 °C

17: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -75 - -55 °C

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1248/cpb.37.1160

Reference yield:

(2S,3R,4R,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-3,4-<1-(4-methoxyphenyl)ethylidenedioxy>heptan-1-ol (114825-77-3) → (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal (124871-71-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 94 percent / oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -60 - -50 °C

2: 99 percent / LDA / tetrahydrofuran / -83 deg C, -20 deg C, 2 h

3: 90 percent / Et₃N / benzene / 0.33 h / 7 °C

4: 99 percent / NaOEt / tetrahydrofuran / 3.5 h / Ambient temperature

5: 78 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

6: m-CPBA / CH₂Cl₂ / 2.5 h / -20 °C

7: 1M n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

8: 46 percent / H₂ / 5percent Pt-C / benzene / 1 h / 8 - 10 °C

9: 84 percent / pyridine / CH₂Cl₂ / 35 h / Ambient temperature

10: 76 percent / 4N HCl / tetrahydrofuran / 13 h / Ambient temperature

11: 91 percent / PPTS / CH₂Cl₂ / 0.42 h / Ambient temperature

12: diisopropylethylamine / CH₂Cl₂ / RT, 45/50 deg C, 12 h

13: 1N NaOH / dioxane / 14 h / 65 - 70 °C

14: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -75 - -55 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1248/cpb.37.1160

Reference yield:

(2S,3R,4R,5R)-2,4-dimethyl-5-(4-methoxybenzyloxy)-3,4-<1-(4-methoxyphenyl)ethylidenedioxy>heptanal (114825-78-4) → (2S,3R,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanal (124871-71-2)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / LDA / tetrahydrofuran / -83 deg C, -20 deg C, 2 h

2: 90 percent / Et₃N / benzene / 0.33 h / 7 °C

3: 99 percent / NaOEt / tetrahydrofuran / 3.5 h / Ambient temperature

4: 78 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

5: m-CPBA / CH₂Cl₂ / 2.5 h / -20 °C

6: 1M n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

7: 46 percent / H₂ / 5percent Pt-C / benzene / 1 h / 8 - 10 °C

8: 84 percent / pyridine / CH₂Cl₂ / 35 h / Ambient temperature

9: 76 percent / 4N HCl / tetrahydrofuran / 13 h / Ambient temperature

10: 91 percent / PPTS / CH₂Cl₂ / 0.42 h / Ambient temperature

11: diisopropylethylamine / CH₂Cl₂ / RT, 45/50 deg C, 12 h

12: 1N NaOH / dioxane / 14 h / 65 - 70 °C

13: oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -75 - -55 °C

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; sodium ethanolate; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; platinum on activated charcoal; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; benzene;

DOI:10.1248/cpb.37.1160

upstream raw materials:

(2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol

(2R,3S,4S,5R,6S,7R)-1-benzoyloxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonane-3,5,6-triol

(2R,3S,4S,5R,6R,7R)-1-benzyloxy-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-2,4,6-trimethylnonan-6-ol

(2R,3S,4S,5R,6R,7R)-1-benzoyloxy-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonane

Downstream raw materials:

(2R,3R,4S,6E,8R,9S,10S,11R,12R,13R)-1-tert-butyldimethylsilyloxy-3-(3,4-dimethoxybenzyloxy)2,4,6,8,10,12-hexamethyl-9,11-isopropylidenedioxy-13-(4-methoxybenzyloxy)-12-methoxymethoxypentadec-6-en-5-one