2α,3α,22α,23α-tetrahydroxy-24β-methyl-B-homo-7-oxa-5α-cholestan-6-one

Base Information

• Chemical Name: 2α,3α,22α,23α-tetrahydroxy-24β-methyl-B-homo-7-oxa-5α-cholestan-6-one
• CAS No.: 113666-77-6
• Molecular Formula: C₂₈H₄₈O₆
• Molecular Weight: 480.686
• Mol file: 113666-77-6.mol

Synonyms:

Chemical Property of 2α,3α,22α,23α-tetrahydroxy-24β-methyl-B-homo-7-oxa-5α-cholestan-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2α,3α,22α,23α-tetrahydroxy-24β-methyl-B-homo-7-oxa-5α-cholestan-6-one

There total 36 articles about 2α,3α,22α,23α-tetrahydroxy-24β-methyl-B-homo-7-oxa-5α-cholestan-6-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: 96.0%

(22R,23R)-22,23-dihydroxy-2α,3α-isopropylidenedioxy-B-homo-7-oxa-5α-campestan-6-one → (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-campestan-6-one (72962-43-7,78821-42-8,78821-43-9,80736-39-6,93860-61-8,93860-62-9,110453-84-4,113666-77-6,135559-12-5,140923-40-6)

Guidance literature:

With acetic acid; In water; at 60 ℃; for 1h;

DOI:10.1039/c4ob02197e

Reference yield:

(R)-2-(1,3-dithian-2-yl)-3-methylbutan-1-ol (1418453-68-5) → (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-campestan-6-one (72962-43-7,78821-42-8,78821-43-9,80736-39-6,93860-61-8,93860-62-9,110453-84-4,113666-77-6,135559-12-5,140923-40-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triethylamine / diethyl ether / 0.25 h / 0 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C / Inert atmosphere

3.2: 0.03 h / -78 °C / Inert atmosphere

4.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; ethanol / 0.08 h / 0 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; potassium bromide / aq. phosphate buffer; dichloromethane / 1.17 h / 0 °C / pH 7 / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / methanol / 0.17 h / 20 °C / Inert atmosphere

9.1: acetic acid / water / 1 h / 60 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; potassium bromide; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c4ob02197e

Reference yield:

isovaleraldehyde (590-86-3) → (22R,23R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-campestan-6-one (72962-43-7,78821-42-8,78821-43-9,80736-39-6,93860-61-8,93860-62-9,110453-84-4,113666-77-6,135559-12-5,140923-40-6)

Guidance literature:

Multi-step reaction with 11 steps

1.1: formic acid / aq. phosphate buffer; toluene / pH 7 / Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 2 h / 0 °C / Inert atmosphere

3.1: triethylamine / diethyl ether / 0.25 h / 0 °C / Inert atmosphere

4.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran / 0.25 h / -78 - 20 °C / Inert atmosphere

5.2: 0.03 h / -78 °C / Inert atmosphere

6.1: sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene / water; ethanol / 0.08 h / 0 °C / Inert atmosphere

7.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / toluene / 0.25 h / -78 °C / Inert atmosphere

9.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium chlorite; potassium bromide / aq. phosphate buffer; dichloromethane / 1.17 h / 0 °C / pH 7 / Inert atmosphere

10.1: pyridinium p-toluenesulfonate / methanol / 0.17 h / 20 °C / Inert atmosphere

11.1: acetic acid / water / 1 h / 60 °C

With 2,6-dimethylpyridine; sodium chlorite; sodium dihydrogenphosphate; lithium aluminium tetrahydride; n-butyllithium; formic acid; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; acetic acid; triethylamine; potassium bromide; In tetrahydrofuran; methanol; aq. phosphate buffer; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c4ob02197e

upstream raw materials:

(R)-2-(1,3-dithian-2-yl)-3-methylbutan-1-ol

isovaleraldehyde