{[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester

Base Information

• Chemical Name: {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester
• CAS No.: 135376-89-5
• Molecular Formula: C₂₆H₃₀FO₈P
• Molecular Weight: 520.492

Synonyms:{[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester

Chemical Property of {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester

There total 4 articles about {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester 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: 71.0%

tetraethyl fluoromethylenebisphosphonate (78715-56-7) + (8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]decan-6-one (98510-27-1) → {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester (135376-89-5)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 10h;

DOI:10.1016/S0040-4039(00)79682-1

Reference yield:

benzyl bromide (100-39-0) → {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester (135376-89-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / NaH / dimethylformamide

2: 81 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

3: 71 percent / lithium diisopropylamide / tetrahydrofuran / 10 h / -78 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79682-1

Reference yield:

myo-inositol monoorthoformate (98510-20-4) → {[(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.13,7]dec-(6E)-ylidene]-fluoro-methyl}-phosphonic acid diethyl ester (135376-89-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 40 percent / NaH / dimethylformamide

2: 81 percent / (COCl)2, DMSO / CH₂Cl₂ / -78 °C

3: 71 percent / lithium diisopropylamide / tetrahydrofuran / 10 h / -78 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79682-1

upstream raw materials:

tetraethyl fluoromethylenebisphosphonate

(8S,9R)-8,9-Bis-benzyloxy-2,4,10-trioxa-tricyclo[3.3.1.1^3,7]decan-6-one

benzyl bromide

myo-inositol monoorthoformate

Downstream raw materials:

[Fluoro-((1R,2S,3R,4R,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid

(3aS,4R,5S,6R,7S,7aS)-3-Fluoro-2-oxo-octahydro-2λ⁵-benzo[d][1,2]oxaphosphole-2,4,5,6,7-pentaol

[Fluoro-((1S,2R,3S,4R,5R,6S)-2,3,4,5,6-pentahydroxy-cyclohexyl)-methyl]-phosphonic acid

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