(13α,21R)-4,4-Dimethyl-15β,8-(epoxymethano)-21-hydroxy-18-nor-16-oxa-5α-androstane-17-one

Base Information

• Chemical Name: (13α,21R)-4,4-Dimethyl-15β,8-(epoxymethano)-21-hydroxy-18-nor-16-oxa-5α-androstane-17-one
• CAS No.: 106009-81-8
• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.456
• Mol file: 106009-81-8.mol

Synonyms:18-Nor-16-oxaandrostane-8-carboxaldehyde,15-hydroxy-4,4-dimethyl-17-oxo-, cyclic 8,15-hemiacetal, [5a,8(R),13a,15b]-; (-)-Dendrillol 1;7H,10H-Furo[2,3,4-cd]naphth[2,1-e]isobenzofuran-7-one,tetradecahydro-10-hydroxy-1,1,4a-trimethyl-, [4aS-(4aa,4bb,6ab,8ab,10a,10aR*,10bb,12ab)]-; Dendrillol 1

Chemical Property of (13α,21R)-4,4-Dimethyl-15β,8-(epoxymethano)-21-hydroxy-18-nor-16-oxa-5α-androstane-17-one

Chemical Property:

• PSA: 55.76000
• LogP: 3.47310

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (13α,21R)-4,4-Dimethyl-15β,8-(epoxymethano)-21-hydroxy-18-nor-16-oxa-5α-androstane-17-one

There total 12 articles about (13α,21R)-4,4-Dimethyl-15β,8-(epoxymethano)-21-hydroxy-18-nor-16-oxa-5α-androstane-17-one 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:

podocarp-8(14)-en-13-one (14022-44-7) → (-)-Dendrillol-1 (106009-81-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / acetone / Irradiation; a) -15 deg C, 2 h, b) -15 deg C to 0 deg C, 0.25 h

3: 1.) HgCl₂/HgO, 2.) NaOMe / 1.) ether, H₂O, r.t., 2 h, 2.) r.t., 30 min

4: 79 percent / SmI₂, pivalic acid, HMPT / tetrahydrofuran / 0.25 h / Ambient temperature

5: 100 percent / 4percent KOH / methanol; H₂O / 72 h / Ambient temperature

6: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2 min, 2.) r.t., 24 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; samarium diiodide; dimethylsulfide; sodium methylate; ozone; mercury dichloride; mercury(II) oxide; Trimethylacetic acid; In tetrahydrofuran; methanol; water; acetone;

DOI:10.1021/jo00051a035

Reference yield:

<3aS-(3aα,5aS,7aα,11aβ,11bα)>-(+)-1,6,7,7a,8,9,10,11,11a,11b-Decahydro-8,8,11a-trimethyl-2H-cyclobutaphenanthren-3(3aH)-one (57710-52-8) → (-)-Dendrillol-1 (106009-81-8)

Guidance literature:

Multi-step reaction with 5 steps

2: 1.) HgCl₂/HgO, 2.) NaOMe / 1.) ether, H₂O, r.t., 2 h, 2.) r.t., 30 min

3: 79 percent / SmI₂, pivalic acid, HMPT / tetrahydrofuran / 0.25 h / Ambient temperature

4: 100 percent / 4percent KOH / methanol; H₂O / 72 h / Ambient temperature

5: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2 min, 2.) r.t., 24 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; samarium diiodide; dimethylsulfide; sodium methylate; ozone; mercury dichloride; mercury(II) oxide; Trimethylacetic acid; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00051a035

Reference yield:

(4aS,4bR,7aS,9aS,11aS)-7-[1-Methoxy-meth-(Z)-ylidene]-1,1,4a-trimethyl-1,3,4,4a,4b,5,6,7,7a,10,11,11a-dodecahydro-2H-cyclobuta[j]phenanthrene → (-)-Dendrillol-1 (106009-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / 60percent HClO₄ / diethyl ether / 0.58 h / 0 °C

2: 18 mg / O₂ / Pt / acetone / 40 °C

3: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, -78 deg C, 2 min, 2.) r.t., 24 h

With perchloric acid; dimethylsulfide; oxygen; ozone; platinum; In diethyl ether; acetone;

DOI:10.1021/jo00051a035

upstream raw materials:

<3R-(3β,3aα,5aR,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carboxylic acid

podocarp-8⁽¹⁴⁾-en-13-one

<3aS-(3aα,5aS,7aα,11aβ,11bα)>-(+)-1,6,7,7a,8,9,10,11,11a,11b-Decahydro-8,8,11a-trimethyl-2H-cyclobutaphenanthren-3(3aH)-one

<3R-(3β,3aα,5aR,7aα,11aβ,11bα)>-(+)-1,3,3a,6,7,7a,8,9,10,11,11a,11b-Dodecahydro-8,8,11a-trimethyl-2H-cyclobutaphenanthrene-3-carbonitrile