(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

Base Information

• Chemical Name: (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
• CAS No.: 137531-90-9
• Molecular Formula: C₄₈H₇₀O₈S₂
• Molecular Weight: 839.211

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 52 articles about (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 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:

C18H21BrMgO3 → (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 (137531-90-9)

Guidance literature:

Multi-step reaction with 9 steps

1: CuI / tetrahydrofuran

2: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

3: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

4: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 86 percent / PPTS / methanol / 36 h / Ambient temperature

6: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

7: 31 percent / aq. KOH; methanol / 24 h / Ambient temperature

8: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 24 h / Ambient temperature

9: 1.) n-butyllithium, tetramethylethylenediamine / 1.) THF, hexane, -20 deg C, 11 h; 2.) -20 deg C, 10 h

With dmap; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; pyridinium p-toluenesulfonate; sodium hydride; copper(l) iodide; In tetrahydrofuran; methanol; potassium hydroxide; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

(2S,3S,4S,5S)-6-(tert-butyldimethylsiloxy)-2,3-epoxy-4-methyl-5-(2-tetrahydropyranyloxy)hexan-1-ol (137531-86-3) → (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 (137531-90-9)

Guidance literature:

Multi-step reaction with 9 steps

1: CuI / tetrahydrofuran

2: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

3: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

4: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

5: 86 percent / PPTS / methanol / 36 h / Ambient temperature

6: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

7: 31 percent / aq. KOH; methanol / 24 h / Ambient temperature

8: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 24 h / Ambient temperature

9: 1.) n-butyllithium, tetramethylethylenediamine / 1.) THF, hexane, -20 deg C, 11 h; 2.) -20 deg C, 10 h

With dmap; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; pyridinium p-toluenesulfonate; sodium hydride; copper(l) iodide; In tetrahydrofuran; methanol; potassium hydroxide; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

3-hydroxy-trans-cinnamic acid (14755-02-3,588-30-7) → (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 (137531-90-9)

Guidance literature:

Multi-step reaction with 17 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: CuI / tetrahydrofuran

10: 93 percent / 4-dimethylaminopyridine / tetrahydrofuran / 12 h / Ambient temperature

11: 62 percent / lithium aluminum hydride / tetrahydrofuran / 14 h / Ambient temperature

12: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

13: 86 percent / PPTS / methanol / 36 h / Ambient temperature

14: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

15: 31 percent / aq. KOH; methanol / 24 h / Ambient temperature

16: 87 percent / NaH / tetrahydrofuran; dimethylformamide / 24 h / Ambient temperature

17: 1.) n-butyllithium, tetramethylethylenediamine / 1.) THF, hexane, -20 deg C, 11 h; 2.) -20 deg C, 10 h

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

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

upstream raw materials:

(2R,3R)-1,2-isopropylidenedioxy-3,5,5-trimethyl-6,6-propylenedithiohexane

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

2,2-dimethyl-4-pentenal

2,2-dimethylpent-4-en-1-ol

Downstream raw materials:

(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

Kishi's aldehyde

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

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