(2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane

Base Information

• Chemical Name: (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane
• CAS No.: 155433-58-2
• Molecular Formula: C₃₆H₄₈O₇
• Molecular Weight: 592.773

Synonyms:(2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane

Chemical Property of (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane

There total 18 articles about (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane 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: 74.0%

p-methoxybenzyl chloride (824-94-2) + (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-3,5-dimethyloctan-4-ol (155433-57-1) → (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane (155433-58-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; for 48h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane (155433-58-2)

Guidance literature:

Multi-step reaction with 12 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: 1.) methylmagnesium bromide / 2.) CuI / 1.) THF, 0 deg C, 5 min.; 2.) THF, -20 deg C, 10 h

10: triethylamine, 4-DMAP / CH₂Cl₂ / 1 h / Ambient temperature

11: lithium aluminum hydride / tetrahydrofuran / 0.08 h / Ambient temperature

12: 74 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; (-)-diisopropyl tartrate; MS 4 Angstroem; methylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81547-7

Reference yield:

3-hydroxy-trans-cinnamic acid (14755-02-3,588-30-7) → (2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane (155433-58-2)

Guidance literature:

Multi-step reaction with 12 steps

2: 92 percent / diisobutyl aluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 90 percent / (-)-diisopropyl tartrate, titanium tetraisopropoxide, t-butyl hydroperoxide, MS 4 Angstroem / CH₂Cl₂; toluene / 11 h / -20 °C

4: 91 percent / Red-al / toluene; tetrahydrofuran / 10.2 h / 0 °C

5: 93 percent / triethylamine, 4-DMAP / CH₂Cl₂ / 4 h / Ambient temperature

6: sodium hydride / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

7: sodium bromide / dimethylformamide / 48 h / Ambient temperature

8: Mg / tetrahydrofuran / 1 h / Irradiation

9: 1.) methylmagnesium bromide / 2.) CuI / 1.) THF, 0 deg C, 5 min.; 2.) THF, -20 deg C, 10 h

10: triethylamine, 4-DMAP / CH₂Cl₂ / 1 h / Ambient temperature

11: lithium aluminum hydride / tetrahydrofuran / 0.08 h / Ambient temperature

12: 74 percent / NaH / tetrahydrofuran; dimethylformamide / 48 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; (-)-diisopropyl tartrate; MS 4 Angstroem; methylmagnesium bromide; sodium hydride; diisobutylaluminium hydride; magnesium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; sodium bromide; copper(l) iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)81547-7

upstream raw materials:

p-methoxybenzyl chloride

(2R,3R,4R,5S,8S)-8--1,2-isopropylidenedioxy-8-methoxy-3,5-dimethyloctan-4-ol

Benzyloxymethyl chloride

3-hydroxy-trans-cinnamic acid

Downstream raw materials:

Kishi's aldehyde

(2R,3R,8S,9S,10R,11S,14S)-14--1,2-isopropylidenedioxy-14-methoxy-10-(p-methoxybenzyloxy)-6,6-propylenedithio-3,5,5,9,11-pentamethyltetradecan-8-yl (3R,4R)-4-benzyloxymethoxy-3-(p-methoxybenzyloxy)pentanoate

(3R,4R)-4-Benzyloxymethoxy-3-(4-methoxy-benzyloxy)-pentanoic acid (1S,2S,3R,4S,7S)-7-(3-benzyloxymethoxy-phenyl)-7-methoxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-1-[2-((R)-1,1,3-trimethyl-4-oxo-butyl)-[1,3]dithian-2-ylmethyl]-heptyl ester

(2R,3R,8S,9S,10R,11S,14S)-14--1,2-isopropylidenedioxy-14-methoxy-10-(p-methoxybenzyloxy)-6,6-propylenedithio-3,5,5,9,11-pentamethyltetra-decan-8-ol

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