<1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

Base Information

• Chemical Name: <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid
• CAS No.: 134932-01-7
• Molecular Formula: C₈H₁₅O₈P
• Molecular Weight: 270.176
• Mol file: 134932-01-7.mol

Synonyms:<1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

Chemical Property of <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid

There total 12 articles about <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid 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:

D-(-)-quinic acid (77-95-2) → <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid (134932-01-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 85 percent / p-toluenesulfonic acid (p-TsOH) / benzene / Heating

2: 75 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

3: 70 percent / p-toluenesulfonic acid (p-TsOH) / dimethylformamide / 24 h / Ambient temperature

4: 79 percent / N-bromosuccinimide (NBS) / benzene / Heating

5: 11 percent / MeONa / tetrahydrofuran; methanol / 0.5 h / Heating

6: 1.) NaH / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 12 h

7: 1.) n-butyllithium, 2.) boron trifluoride etherate

8: 93 percent / 50percent aq. acetic acid / tetrahydrofuran / 5 h / 65 - 75 °C

9: 100 percent / H₂ / 10percent Pd/C / methanol / 2 h / 2585.7 Torr

10: 65 percent / O₂, NaHCO₃ / Pt / H₂O / 8 h / 55 °C

11: 1.) bromotrimethylsilane, trimethylamine, 2.) H₂O / 1.) CH₂Cl₂, RT, 12 h, 2.) RT, 1 h

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; trimethylamine; palladium on activated charcoal; platinum; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00038a002

Reference yield:

<2S-(2α,3aα,5β,7α,7aα)>-hexahydro-5-(hydroxymethyl)-2-phenyl-1,3-benzodioxole-5,7-diol (124561-23-5,141171-57-5) → <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid (134932-01-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / p-toluenesulfonic acid (p-TsOH) / dimethylformamide / 24 h / Ambient temperature

2: 79 percent / N-bromosuccinimide (NBS) / benzene / Heating

3: 11 percent / MeONa / tetrahydrofuran; methanol / 0.5 h / Heating

4: 1.) NaH / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 12 h

5: 1.) n-butyllithium, 2.) boron trifluoride etherate

6: 93 percent / 50percent aq. acetic acid / tetrahydrofuran / 5 h / 65 - 75 °C

7: 100 percent / H₂ / 10percent Pd/C / methanol / 2 h / 2585.7 Torr

8: 65 percent / O₂, NaHCO₃ / Pt / H₂O / 8 h / 55 °C

9: 1.) bromotrimethylsilane, trimethylamine, 2.) H₂O / 1.) CH₂Cl₂, RT, 12 h, 2.) RT, 1 h

With N-Bromosuccinimide; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; trimethylamine; palladium on activated charcoal; platinum; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00038a002

Reference yield:

(3aR,5R,7R,7aS)-5,7-Dihydroxy-2-phenyl-hexahydro-benzo[1,3]dioxole-5-carboxylic acid (141171-64-4) → <1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-(phosphonomethyl)cyclohexane-1-carboxylic acid (134932-01-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / NaBH₄ / ethanol / 0.75 h / 0 °C

2: 70 percent / p-toluenesulfonic acid (p-TsOH) / dimethylformamide / 24 h / Ambient temperature

3: 79 percent / N-bromosuccinimide (NBS) / benzene / Heating

4: 11 percent / MeONa / tetrahydrofuran; methanol / 0.5 h / Heating

5: 1.) NaH / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, 12 h

6: 1.) n-butyllithium, 2.) boron trifluoride etherate

7: 93 percent / 50percent aq. acetic acid / tetrahydrofuran / 5 h / 65 - 75 °C

8: 100 percent / H₂ / 10percent Pd/C / methanol / 2 h / 2585.7 Torr

9: 65 percent / O₂, NaHCO₃ / Pt / H₂O / 8 h / 55 °C

10: 1.) bromotrimethylsilane, trimethylamine, 2.) H₂O / 1.) CH₂Cl₂, RT, 12 h, 2.) RT, 1 h

With sodium tetrahydroborate; N-Bromosuccinimide; n-butyllithium; trimethylsilyl bromide; boron trifluoride diethyl etherate; water; hydrogen; oxygen; sodium methylate; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; trimethylamine; palladium on activated charcoal; platinum; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja00038a002

upstream raw materials:

<1R-(1α,3α,4β,5α)>-1,3,4-trihydroxy-5-<(diisopropoxyphosphinyl)methyl>cyclohexan-1-carboxylic acid

D-(-)-quinic acid

<2S-(2α,3aα,5β,7α,7aα)>-hexahydro-5-(hydroxymethyl)-2-phenyl-1,3-benzodioxole-5,7-diol

<2S-(2α,3aα,5β,7α,7aα)>-hexahydro-7-hydroxy-2',2'-dimethyl-2-phenylspiro<1,3-benzodioxole-5,4'-<1,3>dioxolane>