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

Base Information

• Chemical Name: (2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol
• CAS No.: 124871-55-2
• Molecular Formula: C₂₅H₄₂O₇
• Molecular Weight: 454.604

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 26 articles about (2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol 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) → (2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol (124871-55-2)

Guidance literature:

Multi-step reaction with 16 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

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; 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,4S,5R)-1-benzoyloxy-3,4-dihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane (98003-93-1) → (2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol (124871-55-2)

Guidance literature:

Multi-step reaction with 15 steps

1: CSA / CH₂Cl₂ / 2 h / Ambient temperature

2: 1N KOH / methanol / 18 h / Ambient temperature

3: 94 percent / oxalyl chloride / CH₂Cl₂; dimethylsulfoxide / 0.5 h / -60 - -50 °C

4: 99 percent / LDA / tetrahydrofuran / -83 deg C, -20 deg C, 2 h

5: 90 percent / Et₃N / benzene / 0.33 h / 7 °C

6: 99 percent / NaOEt / tetrahydrofuran / 3.5 h / Ambient temperature

7: 78 percent / LiAlH₄ / diethyl ether / 2 h / 0 °C

8: m-CPBA / CH₂Cl₂ / 2.5 h / -20 °C

9: 1M n-Bu₄NF / tetrahydrofuran / 5 h / Ambient temperature

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

11: 84 percent / pyridine / CH₂Cl₂ / 35 h / Ambient temperature

12: 76 percent / 4N HCl / tetrahydrofuran / 13 h / Ambient temperature

13: 91 percent / PPTS / CH₂Cl₂ / 0.42 h / Ambient temperature

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

15: 1N NaOH / dioxane / 14 h / 65 - 70 °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; 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:

(2R,3S,4S,5R,6R,7R)-1-benzoyloxy-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonane (114825-83-1) → (2R,3S,4S,5R,6R,7R)-3,5-isopropylidenedioxy-7-(4-methoxybenzyloxy)-6-methoxymethoxy-2,4,6-trimethylnonanol (124871-55-2)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 65 - 75 ℃; Yield given;

DOI:10.1016/S0040-4039(00)96566-3

upstream raw materials:

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

(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

(2S,3R,4S,5R)-1,3,4-trihydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylheptane

Downstream raw materials:

(2S,4R)-2-{(4R,5S,6R)-6-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-4-{(4S,5S,6R)-6-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-methoxymethoxy-1-methyl-butyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-pentan-2-ol

(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

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

(2R,3S,4S,5R,6RS,7R,9S,10S,11R,12R,13R)-3,5:9,11-bis(isopropylidenedioxy)-1-tert-butyldiphenylsilyloxy-13-(4-methoxybenzyloxy)-12-methoxymethoxy-2,4,8,10,12-pentamethyl-7-phenylsulfinylpentadecan-6-ol

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