6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione

Base Information

• Chemical Name: 6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione
• CAS No.: 121021-51-0
• Molecular Formula: C20H26O3
• Molecular Weight: 314.425
• DSSTox Substance ID: DTXSID30474290
• Wikidata: Q82304185
• Mol file: 121021-51-0.mol

Synonyms:121021-51-0;6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione;(6R,8R,9S,10R,13S,14S)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-dione;6|A-Hydroxymethylandrosta-1,4-diene-3,17-dione;SCHEMBL135324;DTXSID30474290;CID 11842920;6?-Hydroxymethylandrosta-1,4-diene-3,17-dione;Androsta-1,4-diene-3,17-dione, 6-(hydroxymethyl)-, (6beta)-;6beta-(Hydroxymethyl)androsta-1,4-dien-3,17-dione;Exemestane Impurity B as 6?-Isomer

Chemical Property of 6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione

Chemical Property:

• PSA: 54.37000
• LogP: 3.08180
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 314.18819469
• Heavy Atom Count: 23
• Complexity: 631

Purity/Quality:

98%Min ^*data from raw suppliers

6β-Hydroxymethylandrosta-1,4-diene-3,17-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2=O)CC(C4=CC(=O)C=CC34C)CO
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CCC2=O)C[C@H](C4=CC(=O)C=C[C@]34C)CO
• Uses: 6β-Hydroxymethylandrosta-1,4-diene-3,17-dione is a derivative of Exemestane (E957000) and a potential aromatase inhibitor.

Technology Process of 6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione

There total 4 articles about 6beta-Hydroxymethylandrosta-1,4-diene-3,17-dione 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:

6ξ-hydroxymethyl-4-androstene-3,17-dione (1012054-48-6) → 2,6-hydroxymethyl-1,4-androstadiene-3,17-dione (1012054-49-7) + 6β-hydroxymethylandrosta-1,4-diene-3,17-dione (121021-51-0)

Guidance literature:

Arthrobacter simplex; In water; Product distribution / selectivity; Enzymatic reaction;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 1α,3-dipyrrolidinylandrosta-3,5-dien-17-one (67737-88-6) → 6β-hydroxymethylandrosta-1,4-diene-3,17-dione (121021-51-0)

Guidance literature:

In ethanol; benzene; Yield given; Ambient temperature;

DOI:10.1016/0039-128X(93)90029-M

Reference yield:

Androsta-1,4-diene-3,17-dione (897-06-3) → 6β-hydroxymethylandrosta-1,4-diene-3,17-dione (121021-51-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 20 h / Heating

2: 1.10 g / benzene; ethanol; H₂O / 5 h / 20 °C

In ethanol; water; benzene;

upstream raw materials:

formaldehyd

1α,3-dipyrrolidinylandrosta-3,5-dien-17-one

6ξ-hydroxymethyl-4-androstene-3,17-dione

Androsta-1,4-diene-3,17-dione

Downstream raw materials:

Androsta-1,4-dien-3,6,17-trion

(6S,8R,9S,10R,13S,14S)-6-(methoxymethyl)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-3H-cyclopenta[a]phenanthrene-3,17(6H)-dione

exemestane

Refernces

• 1、 Goelitzer,Bonnekessel,Jones,Palusczak,Hartmann. "Derivatives of exemestane - Synthesis and evaluation of aromatase inhibition". . p. 575 - 581. Retrieved 2007/10/03.