Inhoffen Lythgoe Diol Monotosylate

Base Information

• Chemical Name: Inhoffen Lythgoe Diol Monotosylate
• CAS No.: 66774-80-9
• Molecular Formula: C20H30O4S
• Molecular Weight: 366.522
• Mol file: 66774-80-9.mol

Synonyms:(S,1R,3aR,4S,7aR)-Octahydro-4-hydroxy-,7a-dimethyl-1H-indene-1-ethanol 1-(4-Methylbenzenesulfonate);Inhoffen Lythgoe Diol Monotosylate;1H-Indene-1-ethanol, octahydro-4-hydroxy-b, 7a-diMethyl-1-(4-Methylbenzenesulfonate),(bS, 1R, 3aR, 4S, 7aR)

Chemical Property of Inhoffen Lythgoe Diol Monotosylate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 498.382°C at 760 mmHg
• Flash Point: 255.213°C
• PSA: 103.21000
• Density: 1.17g/cm³
• LogP: 4.14980
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98% ^*data from raw suppliers

Inhoffen lythgoe diol monotosylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Vitamin D analog.

Technology Process of Inhoffen Lythgoe Diol Monotosylate

There total 4 articles about Inhoffen Lythgoe Diol Monotosylate 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: 100.0%

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) + p-toluenesulfonyl chloride (98-59-9) → (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 22h;

Reference yield: 80.0%

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) + toluene-4-sulfonic acid (104-15-4) → (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3)

Guidance literature:

With pyridine; at 0 ℃; for 12h;

DOI:10.1039/c5sc03084f

Reference yield:

Calciferol (50-14-6) → (S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate (66774-80-9,111924-49-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: O₃ / CH₂Cl₂ / -78 °C

1.2: 90 percent / NaBH₄ / methanol / 0 °C

2.1: DMAP / CH₂Cl₂ / 0 °C

With dmap; ozone; In dichloromethane;

DOI:10.1016/j.bmcl.2004.02.076

upstream raw materials:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

p-toluenesulfonyl chloride

Calciferol

toluene-4-sulfonic acid

Downstream raw materials:

des-A,B-8β-[(triethylsilyl)oxy]-22-(p-toluenesulfonyloxy)-23,24-dinorcholane

(S)-2-((1R,3aR,4S,7aR)-4-((tert-butyldimethylsilyl)oxy)-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate

(1R,3aR,4S,7aR)-7a-Methyl-1-((S)-1-methyl-2-phenylsulfanyl-ethyl)-octahydro-inden-4-ol

(S)-2-[(1R,3aR,7aR)-octahydro-7a-methyl-4-oxo-4H-inden-1-yl]propyl 4-methylbenzenesulfonate

Refernces

• 1、 Stambulyan, Hovsep,Minehan, Thomas G.. "A protecting group-free synthesis of (-)-hortonones A-C from the Inhoffen-Lythgoe diol". supporting information. p. 8728 - 8731. Retrieved 2016/10/03.
• 2、 Banerjee, Upasana,Deberardinis, Albert M.,Hadden, M. Kyle. "Design, synthesis, and evaluation of hybrid vitamin D3 side chain analogues as hedgehog pathway inhibitors". . p. 548 - 555. Retrieved 2015/01/30.