Squamocin

Base Information

• Chemical Name: Squamocin
• CAS No.: 120298-30-8
• Deprecated CAS: 129214-51-3
• Molecular Formula: C37H66 O7
• Molecular Weight: 622.927
• DSSTox Substance ID: DTXSID80152793
• Nikkaji Number: J458.692A
• Wikidata: Q27108334
• ChEMBL ID: CHEMBL41177
• Mol file: 120298-30-8.mol

Synonyms:annonin I;squamocin

Chemical Property of Squamocin

Chemical Property:

• Vapor Pressure: 3.8E-27mmHg at 25°C
• Melting Point: 48.5-49 °C
• Refractive Index: 1.508
• Boiling Point: 703.8°Cat760mmHg
• PKA: 14.43±0.20(Predicted)
• Flash Point: 202.4°C
• PSA: 105.45000
• Density: 0.984g/cm³
• LogP: 7.85790
• XLogP3: 9.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 25
• Exact Mass: 622.48085444
• Heavy Atom Count: 44
• Complexity: 801

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCC(CCCC(C1CCC(O1)C2CCC(O2)C(CCCCCCCCCCCCC3=CC(OC3=O)C)O)O)O
• Isomeric SMILES: CCCCCC[C@@H](CCC[C@@H]([C@H]1CC[C@@H](O1)[C@H]2CC[C@@H](O2)[C@@H](CCCCCCCCCCCCC3=C[C@@H](OC3=O)C)O)O)O

Technology Process of Squamocin

There total 19 articles about Squamocin 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: 82.0%

(S)-3-[(R)-13-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-(tert-butyl-dimethyl-silanyloxy)-tridecyl]-5-methyl-5H-furan-2-one (632323-78-5) → squamocin (120298-30-8)

Guidance literature:

With HF (5percent in CH₃CN); In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

Reference yield:

heptanal (111-71-7) → squamocin (120298-30-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: (R)-BINOL; mol sieves 4 Angstroem; Ti(OiPr)4 / CH₂Cl₂ / 1 h / 20 °C

1.2: 68 percent / CH₂Cl₂ / 120 h / -78 - -25 °C

2.1: 98 percent / imidazole / CH₂Cl₂; toluene / 20 °C

3.1: tetrahydrofuran / 18 h / 20 °C

4.1: NaOH; 30percent H₂O₂ / tetrahydrofuran / 5 h

5.1: 82 percent / pyridine / CH₂Cl₂ / 0 °C

6.1: 93 percent / LiBr / tetrahydrofuran / 32 h / 35 °C

7.1: Mg; BrCH₂CH₂Br / diethyl ether / 1 h / 35 °C

7.2: diethyl ether

8.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -20 °C

9.1: 10percent Pd/C / propan-2-ol / 20 °C

10.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 0 °C

11.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

12.1: LDA; LiCl / tetrahydrofuran / 0.5 h / 20 °C

12.2: tetrahydrofuran / 20 °C

13.1: pivaloyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

14.1: LDA / tetrahydrofuran / 0 °C

14.2: tetrahydrofuran / 2 h / 0 - 20 °C

15.1: monoperoxyphthalic acid / tetrahydrofuran; methanol / 0.5 h / 20 °C

16.1: 82 percent / HF (5percent in CH₃CN) / tetrahydrofuran / 6 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; monoperoxyphthalic acid; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; (R)-1,1'-Bi-2-naphthol; pivaloyl chloride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; lithium chloride; lithium bromide; lithium diisopropyl amide; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; toluene; tert-butyl alcohol; 1.1: Addition / 1.2: Substitution / 2.1: silylation / 3.1: Addition / 4.1: Oxidation / 5.1: Tosylation / 6.1: Bromination / 7.1: Metallation / 7.2: Grignard reaction / 8.1: silylation / 9.1: Hydrogenolysis / 10.1: Oxidation / 11.1: Oxidation / 12.1: Metallation / 12.2: Substitution / 13.1: Cyclization / 14.1: Metallation / 14.2: Substitution / 15.1: Oxidation / 16.1: desilylation;

DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

Reference yield:

(S)-(-)-1-decen-4-ol (123464-22-2) → squamocin (120298-30-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 98 percent / imidazole / CH₂Cl₂; toluene / 20 °C

2.1: tetrahydrofuran / 18 h / 20 °C

3.1: NaOH; 30percent H₂O₂ / tetrahydrofuran / 5 h

4.1: 82 percent / pyridine / CH₂Cl₂ / 0 °C

5.1: 93 percent / LiBr / tetrahydrofuran / 32 h / 35 °C

6.1: Mg; BrCH₂CH₂Br / diethyl ether / 1 h / 35 °C

6.2: diethyl ether

7.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -20 °C

8.1: 10percent Pd/C / propan-2-ol / 20 °C

9.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -50 - 0 °C

10.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 20 °C

11.1: LDA; LiCl / tetrahydrofuran / 0.5 h / 20 °C

11.2: tetrahydrofuran / 20 °C

12.1: pivaloyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 20 °C

13.1: LDA / tetrahydrofuran / 0 °C

13.2: tetrahydrofuran / 2 h / 0 - 20 °C

14.1: monoperoxyphthalic acid / tetrahydrofuran; methanol / 0.5 h / 20 °C

15.1: 82 percent / HF (5percent in CH₃CN) / tetrahydrofuran / 6 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; monoperoxyphthalic acid; 2-methyl-but-2-ene; oxalyl dichloride; pivaloyl chloride; magnesium; dimethyl sulfoxide; ethylene dibromide; triethylamine; lithium chloride; lithium bromide; lithium diisopropyl amide; 10percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; isopropyl alcohol; toluene; tert-butyl alcohol; 1.1: silylation / 2.1: Addition / 3.1: Oxidation / 4.1: Tosylation / 5.1: Bromination / 6.1: Metallation / 6.2: Grignard reaction / 7.1: silylation / 8.1: Hydrogenolysis / 9.1: Oxidation / 10.1: Oxidation / 11.1: Metallation / 11.2: Substitution / 12.1: Cyclization / 13.1: Metallation / 13.2: Substitution / 14.1: Oxidation / 15.1: desilylation;

DOI:10.1002/(SICI)1099-0690(200005)2000:10<1889::AID-EJOC1889>3.0.CO;2-R

upstream raw materials:

(S)-3-[(R)-13-{(2R,5R,2'R,5'R)-5'-[(1S,5S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-undecyl]-octahydro-[2,2']bifuranyl-5-yl}-13-(tert-butyl-dimethyl-silanyloxy)-tridecyl]-5-methyl-5H-furan-2-one

heptanal

(S)-(-)-1-decen-4-ol

(4S)-4-tert-butyldimethylsilyloxy-1-decane

Downstream raw materials:

15,24,28-tri-O-(Nα-Boc-Nω-Z-lysyl)squamocin

Refernces

• 1、 Emde, Ulrich,Koert, Ulrich. "Total Syntheses of Squamocin A and Squamocin D". . p. 5979 - 5982. Retrieved 2007/10/03.