(-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide

Base Information

• Chemical Name: (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide
• CAS No.: 1360651-90-6
• Molecular Formula: C₁₃H₁₇FNO₃P
• Molecular Weight: 285.255
• Mol file: 1360651-90-6.mol

Synonyms:(-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide

Chemical Property of (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide

There total 5 articles about (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide 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: 43.0%

cis-1-benzyl-3-(hydroxymethyl)piperidin-4-ol (1135150-45-6) → (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-90-6) + (+)-(1R,3S,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-91-7)

Guidance literature:

With pyridine; phosphoryl dichloride fluoride; In diethyl ether; dichloromethane; at -5 - 0 ℃; Inert atmosphere;

DOI:10.1002/hlca.201100369

Reference yield:

C9H14O3NC6H5 (41276-30-6) → (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-90-6) + (+)-(1R,3S,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-91-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate; sodium carbonate / isopropyl alcohol / 10 °C

1.2: 20 °C

2.1: toluene-4-sulfonic acid / dichloromethane

3.1: Chiralcel_.(R). OD / ethanol; hexane / Resolution of racemate

4.1: hydrogenchloride; water / 60 °C

5.1: pyridine; phosphoryl dichloride fluoride / diethyl ether; dichloromethane / -5 - 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; sodium tetrahydroborate; phosphoryl dichloride fluoride; water; sodium carbonate; toluene-4-sulfonic acid; In diethyl ether; ethanol; hexane; dichloromethane; isopropyl alcohol;

DOI:10.1002/hlca.201100369

Reference yield:

6-benzylhexahydro-2,2-dimethyl-4H-1,3-dioxino[5,4-c]pyridine → (-)-(1R,3R,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-90-6) + (+)-(1R,3S,6R)-8-benzyl-3-fluoro-2,4-dioxa-8-aza-3-phosphadecalin 3-oxide (1360651-91-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Chiralcel_.(R). OD / ethanol; hexane / Resolution of racemate

2: hydrogenchloride; water / 60 °C

3: pyridine; phosphoryl dichloride fluoride / diethyl ether; dichloromethane / -5 - 0 °C / Inert atmosphere

With pyridine; hydrogenchloride; phosphoryl dichloride fluoride; water; In diethyl ether; ethanol; hexane; dichloromethane;

DOI:10.1002/hlca.201100369

upstream raw materials:

6-benzylhexahydro-2,2-dimethyl-4H-1,3-dioxino[5,4-c]pyridine

cis-1-benzyl-3-(hydroxymethyl)piperidin-4-ol

(3RS,4RS)-1-benzyl-3-hydroxymethyl-piperidin-4-ol

C₉H₁₄O₃NC₆H₅