(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

Base Information

• Chemical Name: (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
• CAS No.: 137531-93-2
• Molecular Formula: C₆₅H₈₆O₁₂S₂
• Molecular Weight: 1123.52

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 79 articles about (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 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: 85.0%

(3R,4R)-4-Benzyloxymethoxy-3-(4-methoxy-benzyloxy)-pentanoic acid (1S,2S,3R,4S,7S)-7-(3-benzyloxymethoxy-phenyl)-1-[2-((3R,4R)-4,5-dihydroxy-1,1,3-trimethyl-pentyl)-[1,3]dithian-2-ylmethyl]-7-methoxy-3-(4-methoxy-benzyloxy)-2,4-dimethyl-heptyl ester → (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 (137531-93-2)

Guidance literature:

With lead(IV) acetate; potassium acetate; In acetonitrile; at -20 ℃; for 0.5h;

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

Reference yield:

(2R,3R,4R,5S,8S)-8--1,2-epoxy-8-methoxy-4-(p-methoxybenzyloxy)-3,5-dimethyloctane (110314-58-4) → (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 (137531-93-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 85 percent / 4-dimethylaminopyridine / toluene / 1 h / 50 °C

3: 90 percent / PPTS / methanol / 40 h / Ambient temperature

4: 85 percent / potassium acetate, lead tetraacetate / acetonitrile / 0.5 h / -20 °C

With lead(IV) acetate; dmap; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; potassium acetate; pyridinium p-toluenesulfonate; In methanol; toluene; acetonitrile;

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

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → (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 (137531-93-2)

Guidance literature:

Multi-step reaction with 20 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

18: 85 percent / 4-dimethylaminopyridine / toluene / 1 h / 50 °C

19: 90 percent / PPTS / methanol / 40 h / Ambient temperature

20: 85 percent / potassium acetate, lead tetraacetate / acetonitrile / 0.5 h / -20 °C

With lead(IV) acetate; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; (-)-diisopropyl tartrate; N,N,N,N,-tetramethylethylenediamine; MS 4 Angstroem; potassium acetate; 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; acetonitrile;

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

upstream raw materials:

(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

(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

Benzyloxymethyl chloride

2,2-dimethyl-4-pentenal

Downstream raw materials:

(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

Kishi's aldehyde

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