Leustroducsin B

Base Information

• Chemical Name: Leustroducsin B
• CAS No.: 145142-82-1
• Molecular Formula: C34H56 N O10 P
• Molecular Weight: 669.793
• Mol file: 145142-82-1.mol

Synonyms:leustroducsin B;LSN B

Chemical Property of Leustroducsin B

Chemical Property:

• Vapor Pressure: 1.39E-31mmHg at 25°C
• Boiling Point: 825.3°Cat760mmHg
• Flash Point: 452.9°C
• PSA: 195.65000
• Density: 1.21g/cm³
• LogP: 5.88040
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 21
• Exact Mass: 669.36418398
• Heavy Atom Count: 46
• Complexity: 1100

Purity/Quality:

LEUSTRODUCSIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C=CC(=O)OC1C=CC(CCN)(C(CC(C=CC=CC2CCCC(C2)OC(=O)CCCCC(C)CC)O)OP(=O)(O)O)O
• Isomeric SMILES: CCC1C=CC(=O)OC1/C=C/C(CCN)(C(CC(/C=C/C=C/C2CCCC(C2)OC(=O)CCCCC(C)CC)O)OP(=O)(O)O)O

Technology Process of Leustroducsin B

There total 85 articles about Leustroducsin B 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: 51.0%

(1S,3R)-3-{(1Z,3Z,5R,7R,8R,9E)-8-(2-{[(allyloxyl)carbonyl]amino}ethyl)-7-{[bis(allyloxy)phosphoryl]oxy}-10-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-5-hydroxy-8-[(trimethylsilyl)oxy]deca-1,3,9-trienyl}cyclohexyl (6S)-6-methyloctanoate (521274-48-6) → leustroducsin B (145142-82-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; triethylamine; In tetrahydrofuran; at 50 ℃; for 3h;

DOI:10.1021/ja0340679

Reference yield:

C47H76NO11PSi → leustroducsin B (145142-82-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: aq. CF₃CH₂OH / 1 h / 20 °C

2.1: HF; pyridine / acetonitrile / 8 h / 20 °C

2.2: 49 percent / Ph₃P; HCO₂NH₄; Pd(PPh₃)4 / 7 h / 50 °C

With pyridine; 2,2,2-trifluoroethanol; hydrogen fluoride; In acetonitrile;

DOI:10.1016/j.tetlet.2007.03.152

Reference yield:

(4-hydroxymethyl-2,2-dimethyl-[1,3]-dioxan-4-yl)-methanol (521274-19-1) → leustroducsin B (145142-82-1)

Guidance literature:

Multi-step reaction with 40 steps

1.1: lipase AK / hexane; H₂O / 17 h / 20 °C

1.2: imidazole / dimethylformamide / 1.5 h / 20 °C

2.1: K₂CO₃; MeOH / 2.5 h / 20 °C

3.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

4.1: toluene / 11 h / 100 °C

5.1: DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: imidazole / CH₂Cl₂ / 2 h / 0 °C

8.1: TPAP; NMO; 4 A molecular sieves / CH₂Cl₂ / 3 h / 20 °C

9.1: 8.12 g / diethyl ether / -78 °C

10.1: PPTS / methanol / 0.67 h / 20 °C

11.1: pyridine; DMAP / 6 h / 50 °C

12.1: CSA / dimethylformamide / 0.67 h / 50 °C

13.1: 4.67 g / TBAF / tetrahydrofuran / 1.5 h / 20 °C

14.1: MnO₂ / CH₂Cl₂ / 3 h / 20 °C

15.1: 2.51 g / imidazole / CH₂Cl₂ / 1 h / 20 °C

16.1: n-Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.67 h / 0 °C

16.2: CH₂Cl₂ / 5 h / -78 - 20 °C

17.1: imidazole / dimethylformamide / 0.08 h / 20 °C

18.1: 1.02 g / tetrahydrofuran; hexane / 1.5 h / 0 °C

19.1: DIBAL / toluene / -78 °C

20.1: (n-Bu)4N⁽¹⁺⁾*OH^(1-) / tetrahydrofuran; methanol / 3.5 h / -78 - -18 °C

21.1: PPTS / methanol; tetrahydrofuran / 1 h / 20 °C

22.1: 99 percent / Ti(Oi-Pr)4 / benzene / 0.25 h / 80 °C

23.1: 62 percent / K₂OsO₄*2H₂O; (DHQD)2PHAL; K₃Fe(CN)6 / NaHCO₃ / 2-methyl-propan-2-ol; H₂O / 96 h / 20 °C

24.1: Pb(OAc)4; K₂CO₃ / benzene / 0.08 h / 20 °C

25.1: 400 mg / toluene; diethyl ether; hexane / 3 h / -78 - -10 °C

26.1: Zn; LiCuBr₂ / ethanol / 0.33 h / 80 °C

27.1: 364 mg / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

28.1: ZnBr₂; Et₃SiH / CH₂Cl₂ / 2 h / -18 °C

28.2: 68 percent / PPTS / methanol; tetrahydrofuran / 0.17 h / 20 °C

29.1: 73 percent / HN₃; PPh₃; DEAD / toluene / 0.17 h / 0 °C

30.1: PPh₃; water / tetrahydrofuran / 22 h / 20 °C

31.1: 48.5 mg / pyridine / tetrahydrofuran / 0.17 h / 20 °C

32.1: (HF)3*NEt₃ / tetrahydrofuran / 0.67 h / 20 °C

33.1: 22.0 mg / aq. AcOH / tetrahydrofuran / 10 h / 20 °C

34.1: pyridine / 4 h / 20 °C

35.1: 16.8 mg / (HF)3*NEt₃ / tetrahydrofuran / 3 h / 20 °C

36.1: 1H-tetrazole / acetonitrile; CH₂Cl₂ / 0.33 h / 20 °C

36.2: 79 percent / t-BuOOH / CH₂Cl₂; acetonitrile; decane / 1 h / 0 °C

37.1: 82 percent / CAN / tetrahydrofuran; H₂O / 0.08 h / 0 °C

38.1: 92 percent / DCC; DMAP / toluene / 1 h / 20 °C

39.1: 68 percent / Er(OTf)3 / methanol / 2.5 h / 20 °C

40.1: 51 percent / HCO₂H; Et₃N; Pd(PPh₃)4 / tetrahydrofuran / 3 h / 50 °C

With pyridine; 1H-imidazole; 1H-tetrazole; lead(IV) acetate; titanium(IV) isopropylate; methanol; triethylsilane; dmap; manganese(IV) oxide; potassium osmate(VI); tetrakis(triphenylphosphine) palladium⁽⁰⁾; formic acid; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; lipase AK; tris-(2-chloro-ethyl)-amine; Br₂Cu^(1-)*Li⁽¹⁺⁾; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine tris(hydrogen fluoride); 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; zinc dibromide; potassium hexacyanoferrate(III); zinc; diethylazodicarboxylate; erbium(III) triflate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene; 4.1: Wittig reaction;

DOI:10.1021/ja0340679

upstream raw materials:

(1S,3R)-3-{(1Z,3Z,5R,7R,8R,9E)-8-(2-{[(allyloxyl)carbonyl]amino}ethyl)-7-{[bis(allyloxy)phosphoryl]oxy}-10-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-5-hydroxy-8-[(trimethylsilyl)oxy]deca-1,3,9-trienyl}cyclohexyl (6S)-6-methyloctanoate

(2R,3S)-3-ethyl-6-(4-methoxybenzyloxy)-4-hexyne-1,2-diol

(2R,3S)-3-ethyl-1,2-(4-methoxybenzylidenedioxy)-6-(4-methoxybenzyloxy)-4-hexyne

C₂₄H₃₀O₅

Downstream raw materials:

(S)-6-Methyl-octanoic acid (1S,3R)-3-[(1Z,3Z,9E)-(5R,7R,8R)-8-(2-allyloxycarbonylamino-ethyl)-10-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-5,7,8-trihydroxy-deca-1,3,9-trienyl]-cyclohexyl ester

(S)-6-Methyl-octanoic acid (1S,3R)-3-((1Z,3Z)-4-{(4R,6R)-6-[(E)-(R)-1-(2-allyloxycarbonylamino-ethyl)-3-((2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-hydroxy-allyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-buta-1,3-dienyl)-cyclohexyl ester

(6S)-6-methyloctanoic acid

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