Salicylihalamide A

Base Information

• Chemical Name: Salicylihalamide A
• CAS No.: 198481-99-1
• Molecular Formula: C26H33NO5
• Molecular Weight: 439.552
• Mol file: 198481-99-1.mol

Synonyms:salicylhalamide A;salicylihalamide A;(2Z,4Z)-Hepta-2,4-dienoic acid [(E)-3-((E)-(7S,9R,10S)-4,9-dihydroxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro-5H-6-oxa-benzocyclododecen-7-yl)-propenyl]-amide;

Chemical Property of Salicylihalamide A

Chemical Property:

• Vapor Pressure: 4.67E-21mmHg at 25°C
• Boiling Point: 708.3°Cat760mmHg
• Flash Point: 382.2°C
• PSA: 95.86000
• Density: 1.111g/cm³
• LogP: 4.74040

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Salicylihalamide A

There total 121 articles about Salicylihalamide A 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: 78.0%

bis[teri-butyl(dimethyl)silyl]-salicylihalamide (350794-14-8) → (-)-salicylihalamide A (198481-99-1,198482-00-7)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; for 72h;

DOI:10.1021/ol015822v

Reference yield:

2-allyl-6-methoxy-benzoic acid (325172-28-9) → (-)-salicylihalamide A (198481-99-1,198482-00-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 84 percent / triphenylphosphine; diethyl azodicarboxylate / benzene / 24 h

2: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / 0.67 h / 20 °C

3: 98 percent / DDQ; buffer / CH₂Cl₂; H₂O / 0.75 h / 20 °C / pH 7

4: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

5: 82 percent / BBr₃ / CH₂Cl₂ / 3 h / -78 °C

6: 97 percent / sodium chlorite; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h

7: triethylamine / CH₂Cl₂ / 2 h / 20 °C

8: 21 mg / K₂CO₃; H₂O / methanol; tetrahydrofuran / 0.08 h / 20 °C

9: N,N-diisopropylethylamine / acetone / 0 - 20 °C

10: sodium azide / acetone; H₂O / 0.5 h / 20 °C

11: toluene / 0.25 h / 110 °C

12: 21.6 mg / toluene / 0.17 h / Heating

13: 81 percent / sodium bis(trimethylsilyl)amide / tetrahydrofuran; benzene / 0.17 h / 0 °C

14: tetrabutylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

15: 2.6 mg / HF*py / tetrahydrofuran; pyridine / 48 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; sodium azide; 2-methyl-but-2-ene; tetrabutyl ammonium fluoride; water; sodium hexamethyldisilazane; boron tribromide; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetone; toluene; tert-butyl alcohol; benzene; 1: Mitsunobu esterification / 2: ring closing metathesis / 4: Dess-Martin oxidation / 11: Curtius rearrangement;

DOI:10.1016/S0040-4020(02)00657-9

Reference yield:

(7S,9R,10S,12E)-(4-methoxy-9-methoxymethoxy-10-methyl-5-oxo-7,8,9,10,11,14-hexahydro[5H]-6-oxa-benzocyclododecen-7-yl)-acetaldehyde (398478-59-6) → (-)-salicylihalamide A (198481-99-1,198482-00-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

2.1: 64 percent / BBr₃ / CH₂Cl₂ / 0.33 h / -78 °C

3.1: Ba(OH)2*8H₂O / tetrahydrofuran / 20 °C

4.1: imidazole; DMAP / dimethylformamide / 20 °C

5.1: 92 percent / (PhO)2P(O)N₃; Et₃N / benzene / 14 h / 20 °C

6.1: benzene / 6 h / 75 °C

7.1: t-BuLi / tetrahydrofuran / 0.75 h / -78 °C

7.2: 5.9 mg / tetrahydrofuran; diethyl ether / 1 h / -78 - 0 °C

8.1: HF; pyridine / tetrahydrofuran / 48 h / 20 °C

With pyridine; 1H-imidazole; dmap; barium dihydroxide; diphenyl phosphoryl azide; hydrogen fluoride; tert.-butyl lithium; boron tribromide; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Horner-Wadsworth-Emmons homologation / 5.1: 7 / 6.1: Curtius rearrangement;

DOI:10.1021/ja0177713

upstream raw materials:

(1Z,3Z/E)-1-bromo-1,3-hexadiene

(E)-(7S,9R,10S)-4,9-Bis-(tert-butyl-dimethyl-silanyloxy)-7-((E)-3-isocyanato-allyl)-10-methyl-7,8,9,10,11,14-hexahydro-6-oxa-benzocyclododecen-5-one

bis[teri-butyl(dimethyl)silyl]-salicylihalamide

(2Z,4Z)-hepta-2,4-dienoic acid amide

Refernces

• 1、 Wu,Seguil,De Brabander. "Synthesis and initial structure--activity relationships of modified salicylihalamides.". . p. 4241 - 4244. Retrieved 2000.
• 2、 Herb, Christian,Bayer, Alexander,Maier, Martin E.. "Total synthesis of salicylihalamides A and B". . p. 5649 - 5660. Retrieved 2007/10/03.
• 3、 Wu, Yusheng,Liao, Xibin,Wang, Ruifang,Xie, Xiao-Song,De Brabander, Jef K.. "Total synthesis and initial structure - Function analysis of the potent V-ATPase inhibitors salicylihalamide A and related compounds". . p. 3245 - 3253. Retrieved 2007/10/03.