lasalocid benzyl ester

Base Information

• Chemical Name: lasalocid benzyl ester
• CAS No.: 41733-86-2
• Molecular Formula: C₄₁H₆₀O₈
• Molecular Weight: 680.923
• Mol file: 41733-86-2.mol

Synonyms:lasalocid benzyl ester

Chemical Property of lasalocid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of lasalocid benzyl ester

There total 47 articles about lasalocid benzyl 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: 33.8%

3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester (67045-68-5) + 4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one (31478-26-9,87678-18-0) → lasalocid benzyl ester (41733-86-2)

Guidance literature:

With zinc(II) chloride; lithium diisopropyl amide; In diethyl ether; at 0 ℃; Further byproducts given;

DOI:10.1021/ja00345a055

Reference yield:

2-(dibenzylamino)-3-methyl-6-(3(R)-methyl-4-pentenyl)benzoic acid methyl ester (75371-80-1) → lasalocid benzyl ester (41733-86-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / 4-methylmorpholine 4-oxide, OsO₄ / H₂O; 2-methyl-propan-2-ol / 24 h / Ambient temperature

2: 93 percent / H₂ / Pd/C / ethanol / 10 h / 2585.7 Torr

3: 85 percent / HBF₄, isoamyl nitrite / ethanol / 0.5 h / 0 °C

4: 98 percent / p-toluenesulfonic acid / acetone / 0.25 h / Ambient temperature

5: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h

6: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h

7: 10percent HCl / H₂O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h

8: 80 percent / NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

9: 33.8 percent / LDA, ZnCl₂ / diethyl ether / 0 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; tetrafluoroboric acid; n-butyllithium; 1-thiopropane; hydrogen; potassium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; zinc(II) chloride; lithium diisopropyl amide; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja00345a055

Reference yield:

benzyl 2(S)-<5(S)-carbomethoxy-3(S)-methyl-5-(5,6-dihydro)-5(S)-(methoxymethylenoxy)-6(S)-methyl-2(R)-pyranyl-2(S)-tetrahydrofuryl>butyl ether (84985-06-8) → lasalocid benzyl ester (41733-86-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 85 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

2: 95 percent / DIBAL / diethyl ether; hexane / 1 h / -78 °C

3: 88 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

4: 90 percent / H₂ / Ni(Ra) / ethyl acetate / 3 h / Ambient temperature

5: 100 percent / 10percent HCl / tetrahydrofuran; H₂O / 16 h / 50 °C

6: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature

7: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h

8: NaHCO₃, MCPBA / CH₂Cl₂ / 3 h / Ambient temperature

9: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h

10: 98 percent / Li, NH₃ / tetrahydrofuran / 1 h / Heating

11: 78 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 2 h

12: 89 percent / tetrahydrofuran / 0.5 h / 0 °C

13: 90 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 2 h

14: 33.8 percent / LDA, ZnCl₂ / diethyl ether / 0 °C

With hydrogenchloride; copper(l) iodide; n-butyllithium; oxalyl dichloride; ammonia; hydrogen; sodium acetate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; Ni(Ra); In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; ethyl acetate; pentane;

DOI:10.1021/ja00345a055

upstream raw materials:

3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one

benzyl bromide

lasalocid sodium

Downstream raw materials:

6-[(R)-3-((2R,3S)-3-{(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyryl}-3-methyl-oxiranyl)-butyl]-2-hydroxy-3-methyl-benzoic acid benzyl ester

6-[(R)-3-((2S,3R)-3-{(R)-2-[(2S,3S,5S)-5-Ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-butyryl}-3-methyl-oxiranyl)-butyl]-2-hydroxy-3-methyl-benzoic acid benzyl ester

Lithium; 6-{(3R,4R,5R,7R)-7-[(2S,3S,5S)-5-ethyl-5-((2R,5R,6S)-5-ethyl-5-hydroxy-6-methyl-tetrahydro-pyran-2-yl)-3-methyl-tetrahydro-furan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxo-nonyl}-2-hydroxy-3-methyl-benzoate

lithium lasalocid

Refernces

• 1、 Noda,Horita,Oikawa,Yonemitsu. "Stereoselective synthesis of polyether antibiotics, lasalocid A and isolasalocid A, via a chelation-controlled formation of tetrahydrofuran rings under thermodynamic conditions". . p. 6035 - 6038. Retrieved 2007/10/02.