24R-methylcalciol

Base Information

• Chemical Name: 24R-methylcalciol
• CAS No.: 71761-06-3
• Molecular Formula: C29H48O
• Molecular Weight: 412.7
• UNII: 0W2I161LCL
• DSSTox Substance ID: DTXSID301028171
• Nikkaji Number: J39.466A
• Wikipedia: Vitamin_D5
• Mol file: 71761-06-3.mol

Synonyms:24R-methylcalciol;Vitamin D5;71761-06-3;UNII-0W2I161LCL;0W2I161LCL;(5Z,7E)-9,10-Secostigmasta-5,7,10(19)-trien-3beta-ol;9,10-Secostigmasta-5,7,10(19)-trien-3-ol, (3beta,5Z,7E)-;(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexan-1-ol;(3beta,5Z,7E)-9,10-secostigmasta-5,7,10(19)-trien-3-ol;SITOCALCIFEROL [WHO-DD];CHEBI:33279;DTXSID301028171;C18193;(3S,5Z,7E)-9,10-secostigmasta-5,7,10-trien-3-ol;9,10-SECOSTIGMASTA-5,7,10(19)-TRIEN-3-OL, (3.BETA.,5Z,7E)-;CYCLOHEXANOL, 5-((2E)-2-((1R,3AS,7AR)-1-((1R,4R)-4-ETHYL-1,5-DIMETHYLHEXYL)OCTAHYDRO-7A-METHYL-4H-INDEN-4-YLIDENE)ETHYLIDENE)-4-METHYLENE-, (1S,5Z)-

Chemical Property of 24R-methylcalciol

Chemical Property:

• Vapor Pressure: 7.52E-13mmHg at 25°C
• Melting Point: 105-106 °C
• Boiling Point: 517°Cat760mmHg
• PKA: 14.74±0.20(Predicted)
• Flash Point: 225.1°C
• PSA: 20.23000
• Density: 0.96g/cm³
• LogP: 8.25510
• XLogP3: 8.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 7
• Exact Mass: 412.370516150
• Heavy Atom Count: 30
• Complexity: 653

Purity/Quality:

99% ^*data from raw suppliers

VitaminD5 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C)C(C)C
• Isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C)C(C)C
• Uses: Vitamin D5 is used in the synthetic preparation of 1α-Hydroxyvitamin D5 a promising chemopreventive agent for breast cancer.

Technology Process of 24R-methylcalciol

There total 14 articles about 24R-methylcalciol 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: 40.0%

previtamin D5 → 9,10-seco-stigmasta-5(Z),7(E),10(19)-trien-3β-ol (71761-06-3)

Guidance literature:

In ethanol; at 60 ℃; for 4h;

Reference yield:

Acetic acid (S)-3-[2-[(1R,3aS,7aR)-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-octahydro-inden-(4E)-ylidene]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (865539-85-1) → 9,10-seco-stigmasta-5(Z),7(E),10(19)-trien-3β-ol (71761-06-3)

Guidance literature:

With sodium hydroxide; In methanol; water; at 20 ℃; for 3h;

DOI:10.1021/jo050853f

Reference yield:

Acetic acid (S)-3-{(Z)-2-[(1R,3aR,7aR)-1-((1R,4R)-4-ethyl-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methyl-cyclohex-3-enyl ester → 9,10-seco-stigmasta-5(Z),7(E),10(19)-trien-3β-ol (71761-06-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ethyl acetate / Heating

2: 2.6 g / sodium hydroxide / methanol; H₂O / 3 h / 20 °C

With sodium hydroxide; In methanol; water; ethyl acetate;

DOI:10.1021/jo050853f

upstream raw materials:

stigmastadien-(5.7)-ol-(3β)

benzene

5-stigmasten-3β,7β-diol

3β,7β-dibenzoyloxy-stigmastene-(5)

Downstream raw materials:

9,10-seco-stigmasta-5(E),7(E),10(19)-trien-3β-ol

3β-triethylsilyloxy-9,10-seco-stigmasta-5(E),7(E),10(19)-triene

Refernces

• 1、 -. "1α-Hydroxyvitamin D5, its synthesis and use in cancer prevention". Page/Page column Sheet 2; 4. . Retrieved 2010/02/11.