(R)-2-[(2R)-Decahydro-8aβ-hydroxy-4aα-methyl-8-methylenenaphthalen-2-yl]-1,2-propanediol

Base Information

• Chemical Name: (R)-2-[(2R)-Decahydro-8aβ-hydroxy-4aα-methyl-8-methylenenaphthalen-2-yl]-1,2-propanediol
• CAS No.: 77521-40-5
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37
• Mol file: 77521-40-5.mol

Synonyms:(R)-2-((2R,4aR,8aR)-8a-Hydroxy-4a-methyl-8-methylene-decahydro-naphthalen-2-yl)-propane-1,2-diol;kutdtriol;kudtriol;

Chemical Property of (R)-2-[(2R)-Decahydro-8aβ-hydroxy-4aα-methyl-8-methylenenaphthalen-2-yl]-1,2-propanediol

Chemical Property:

• PSA: 60.69000
• LogP: 2.00730

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(2R)-Decahydro-8aβ-hydroxy-4aα-methyl-8-methylenenaphthalen-2-yl]-1,2-propanediol

There total 14 articles about (R)-2-[(2R)-Decahydro-8aβ-hydroxy-4aα-methyl-8-methylenenaphthalen-2-yl]-1,2-propanediol 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:

(+)-2-(1,2,3,4,4a,5,6,7-octahydro-4a,8-dimethyl-7-oxo-2-naphthyl)-propionic acid (3466-64-6) → kudtriol (77521-40-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 91 percent / conc. HCl / 1.5 h / Heating

2: 92.3 percent / BF₃*Et₂O / methanol / 4 h / 0 - 5 °C

3: 65 percent / Raney Ni / propan-2-ol / 10 deg C, 30 min, then 40 deg C, 2 h

4: 86.2 percent / DIBAL (20 percent toluene) / tetrahydrofuran / -78 deg C, 1 h, then to 0 deg C

5: 51.5 percent / CrO₃ supported on silica / CH₂Cl₂ / addition, 10 deg C, 2 h, then 1 h

6: 1.) BuLi, (i-Pr)2NH, 3.) MoOPH / 1.) THF, hexane, -20 deg C, 10 min, 2.) THF, hexane, -78 deg C, to -50 deg C, 20 min, -50 deg C, 30 min, 3.) THF, hexane

7: 51 percent / DIBAL (toluene) / tetrahydrofuran / -70 deg C 30 min, then 0 deg C 15 min

8: O₂ / methylene blue / ethanol / 9 h / Irradiation

9: NaBH₄ / ethanol / 0.5 h

With sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; CrO₃/silica gel; boron trifluoride diethyl etherate; oxygen; nickel; diisobutylaluminium hydride; diisopropylamine; hydrogenchloride; methylene blue; In tetrahydrofuran; methanol; ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1039/P19880003149

Reference yield:

(+)-5α-hydroxy-β-selinene (119967-73-6) → kudtriol (77521-40-5)

Guidance literature:

With AD-mix-β; In water; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1016/S0957-4166(00)00119-1

Reference yield:

methyl (11S)-3,3-ethylenedithioeudesm-4-en-12-oate (122442-38-0) → kudtriol (77521-40-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / Raney Ni / propan-2-ol / 10 deg C, 30 min, then 40 deg C, 2 h

2: 86.2 percent / DIBAL (20 percent toluene) / tetrahydrofuran / -78 deg C, 1 h, then to 0 deg C

3: 51.5 percent / CrO₃ supported on silica / CH₂Cl₂ / addition, 10 deg C, 2 h, then 1 h

4: 1.) BuLi, (i-Pr)2NH, 3.) MoOPH / 1.) THF, hexane, -20 deg C, 10 min, 2.) THF, hexane, -78 deg C, to -50 deg C, 20 min, -50 deg C, 30 min, 3.) THF, hexane

5: 51 percent / DIBAL (toluene) / tetrahydrofuran / -70 deg C 30 min, then 0 deg C 15 min

6: O₂ / methylene blue / ethanol / 9 h / Irradiation

7: NaBH₄ / ethanol / 0.5 h

With sodium tetrahydroborate; n-butyllithium; MoO₅*pyridine*HMPA; CrO₃/silica gel; oxygen; nickel; diisobutylaluminium hydride; diisopropylamine; methylene blue; In tetrahydrofuran; ethanol; dichloromethane; isopropyl alcohol;

DOI:10.1039/P19880003149

upstream raw materials:

eudesm-4-ene-11,12-diol

(R)-2-((2R,4aR,8aR)-8a-Hydroperoxy-4a-methyl-8-methylene-decahydro-naphthalen-2-yl)-propane-1,2-diol

(+)-5α-hydroxy-β-selinene

eudesma-4,11-dien-3-one

Refernces

• 1、 Zhou, Gang,Gao, Xiaolei,Zhang, Zhe,Li, Weidong Z.,Li, Yulin. "Enantioselective total syntheses of kudtriol, 5-epi-kudtriol and their C-11 epimers". . p. 1819 - 1826. Retrieved 2000.