(1R)-2,4,4aβ,5,6,7,7aβ,7b-Octahydro-3-hydroxymethyl-6,6,7bα-trimethyl-1H-cyclobut[e]indene-1,4α-diol

Base Information

• Chemical Name: (1R)-2,4,4aβ,5,6,7,7aβ,7b-Octahydro-3-hydroxymethyl-6,6,7bα-trimethyl-1H-cyclobut[e]indene-1,4α-diol
• CAS No.: 16981-75-2
• Molecular Formula: C₁₅H₂₄O₃
• Molecular Weight: 252.354
• Mol file: 16981-75-2.mol

Synonyms:1H-Cyclobut[e]indene-1,4-diol,2,4,4a,5,6,7,7a,7b-octahydro-3-(hydroxymethyl)-6,6,7b-trimethyl-, [1R-(1a,4a,4ab,7ab,7ba)]-; 1H-Cyclobut[e]indene-1,4-diol, 2,4,4aa,5,6,7,7aa,7b-octahydro-3-(hydroxymethyl)-6,6,7bb-trimethyl- (8CI); Illudol

Chemical Property of (1R)-2,4,4aβ,5,6,7,7aβ,7b-Octahydro-3-hydroxymethyl-6,6,7bα-trimethyl-1H-cyclobut[e]indene-1,4α-diol

Chemical Property:

• PSA: 60.69000
• LogP: 1.47310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R)-2,4,4aβ,5,6,7,7aβ,7b-Octahydro-3-hydroxymethyl-6,6,7bα-trimethyl-1H-cyclobut[e]indene-1,4α-diol

There total 32 articles about (1R)-2,4,4aβ,5,6,7,7aβ,7b-Octahydro-3-hydroxymethyl-6,6,7bα-trimethyl-1H-cyclobut[e]indene-1,4α-diol 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: 74.0%

(1S,4S,4aS,7aR,7bS)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxymethyl-6,6,7b-trimethyl-2,4,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]inden-4-ol → (+/-)-illudol (16981-75-2,34175-73-0,125356-84-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 12h;

DOI:10.1021/ja00001a067

Reference yield:

1-(4,4-dimethyl-1-cyclopenten-1-yl)ethanone (73011-50-4) → (+/-)-illudol (16981-75-2,34175-73-0,125356-84-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -78 deg C, 6h, 2.) 25 deg C, 15 min

2: 72 percent / 240 h / 48 °C

3: 96 percent / methanol / 5.4 h / 25 °C / Linde 3-Angstroem molecular sieves

4: 1.) lithium triethylborohydride, 2.) sodium hydride / 1.) THF, 25 deg C, 3 min, 2.) THF, reflux, 5 h

5: 96 percent / lithium aluminium hydride / diethyl ether / 2 h / 0 °C

6: 82 percent / n-butyllithium, tetramethylenediamine / tetrahydrofuran; hexane / 3 h / 25 °C

7: 94 percent / lithium, ethylamine, tert-butyl alcohol / tetrahydrofuran / 1 h / 0 °C

8: 87 percent / chromium trioxide, pyridine / CH₂Cl₂ / 2.5 h / 25 °C

9: 1.) lithium diisopropylamide / 1.) THF, -58 deg C, 50 min, 2.) ether, 5 min

10: 437 mg / lithium diisopropylamine / tetrahydrofuran / 0.17 h

11: 96 percent / 15percent aq. hydrogen peroxide / CH₂Cl₂ / 0.33 h / 25 °C

12: 1.) Red-al, p-toluenesulfonic acid

With pyridine; chromium(VI) oxide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; lithium; sodium hydride; lithium triethylborohydride; toluene-4-sulfonic acid; ethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane;

DOI:10.1021/ja00367a018

Reference yield:

tert-Butyl-[1-(4,4-dimethyl-cyclopent-1-enyl)-vinyloxy]-dimethyl-silane (76221-45-9) → (+/-)-illudol (16981-75-2,34175-73-0,125356-84-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 72 percent / 240 h / 48 - 50 °C

2: 97 percent / lithium aluminium hydride / diethyl ether / 0.5 h / 0 °C

3: 86 percent / sodium hydride, tetramethylethylenediamine / 1,2-dimethoxy-ethane / 20 h / 55 °C

4: 90 percent / lithium, ethylamine / 2 h / -78 °C

5: 56 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 0.33 h / 0 °C

6: 1.) lithium diisopropylamide / 1.) THF, -58 deg C, 50 min, 2.) ether, 5 min

7: 437 mg / lithium diisopropylamine / tetrahydrofuran / 0.17 h

8: 96 percent / 15percent aq. hydrogen peroxide / CH₂Cl₂ / 0.33 h / 25 °C

9: 1.) Red-al, p-toluenesulfonic acid

With lithium aluminium tetrahydride; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium; sodium hydride; toluene-4-sulfonic acid; ethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane;

DOI:10.1021/ja00367a018

upstream raw materials:

1,4,4-trimethyl-1-cyclohexene

1-(4,4-dimethyl-1-cyclopenten-1-yl)ethanone

tert-Butyl-[1-(4,4-dimethyl-cyclopent-1-enyl)-vinyloxy]-dimethyl-silane

(2aS,4R,4aS,7aR,7bR)-1,1-Diethoxy-6,6,7b-trimethyl-decahydro-cyclobuta[e]inden-4-ol

Refernces

• 1、 Semmelhack, M.F.,Tomoda, Shuji,Hurst, K.M.. "Synthesis of (+/-)-Illudol". . p. 7567 - 7568. Retrieved 2007/10/02.