Spirosolan-3-ol

Base Information

• Chemical Name: Spirosolan-3-ol
• CAS No.: 77-59-8
• Molecular Formula: C27H45 N O2
• Molecular Weight: 415.66
• NSC Number: 226903,224427
• DSSTox Substance ID: DTXSID50859106
• Wikidata: Q105344582
• Mol file: 77-59-8.mol

Synonyms:soladulcidine;spirosolan-3-ol

Chemical Property of Spirosolan-3-ol

Chemical Property:

• Vapor Pressure: 2.56E-13mmHg at 25°C
• Melting Point: 210.5℃
• Refractive Index: 1.6840 (estimate)
• Boiling Point: 527.2°C at 760 mmHg
• PKA: 15.14±0.70(Predicted)
• Flash Point: 272.7°C
• PSA: 41.49000
• Density: 1.1g/cm³
• LogP: 5.69560
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 415.345029678
• Heavy Atom Count: 30
• Complexity: 696

Purity/Quality:

99% ^*data from raw suppliers

Tomatidine ^*data from reagent suppliers

Safty Information:

• Statements: 23/25
• Safety Statements: 1-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1

Technology Process of Spirosolan-3-ol

There total 21 articles about Spirosolan-3-ol 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: 95.0%

tomatidine acetate (66934-60-9) → tomatidine (77-59-8)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; water; at 23 ℃; for 2h; Inert atmosphere;

DOI:10.1002/ejoc.202000051

Reference yield: 80.0%

dihydrotomatidine A (1667-29-4) → tomatidine (77-59-8)

Guidance literature:

With manganese(IV) oxide; In chloroform; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(00)93648-7

Reference yield:

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-azido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1Hnaphtho[2',1':4,5]indeno[2,1-b]furan-4-yl acetate → soladulcidine (511-98-8) + tomatidine (77-59-8)

Guidance literature:

(2aS,4S,6aS,6bS,8aS,8bS,11aS,12aS,12bR)-10-((S)-4-azido-3-methylbutyl)-6a,8a,9-trimethyl-2,2a,3,4,5,6,6a,6b,7,8,8a,8b,11a,12,12a,12b-hexadecahydro-1Hnaphtho[2',1':4,5]indeno[2,1-b]furan-4-yl acetate; With chloro-trimethyl-silane; sodium iodide; In acetonitrile; at 23 ℃; for 1h;

With sodium hydroxide; In methanol; dichloromethane; at 23 ℃; for 2h;

DOI:10.3390/molecules26196008

upstream raw materials:

dihydrotomatidine A

N-Chlorotomatidine

trifluoroacetic acid

tomatine

Downstream raw materials:

demissidine

tomatidine acetate

O,N-Diacetyl-tomatidin

Refernces

• 1、 Tukalo,Ivanchenko. "-". . . Retrieved 1971.
• 2、 Quyen, Le Thi,Himmelreich, Uwe,Schreiber, Klaus. "Solanum alkaloids, 139: Photolysis of N-chlorospirosolanes". . p. 1589 - 1592. Retrieved 1997.
• 3、 Sato et al.. "-". . p. 538. Retrieved 1952.
• 4、 Normandin, Chad,Malouin, Fran?ois,Marsault, Eric. "Gram-Scale Synthesis of Tomatidine, a Steroid Alkaloid with Antibiotic Properties Against Persistent Forms of Staphylococcus aureus". . p. 2693 - 2698. Retrieved 2020/05/04.