Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester

Base Information

• Chemical Name: Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester
• CAS No.: 104846-25-5
• Molecular Formula: C₂₇H₃₃O₁₅P₃
• Molecular Weight: 690.471
• Mol file: 104846-25-5.mol

Synonyms:Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester

Chemical Property of Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester

There total 18 articles about Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) 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:

2,3,6-tris-O-(phenylmethyl)-D-myo-inositol (104873-76-9) → Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester (104846-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-tetrazole / CH₂Cl₂ / 45 h

2: 291 mg / mCPBA / CH₂Cl₂ / -78 - 20 °C

3: triethylamine / CH₂Cl₂ / 16 h / 20 °C

With 1H-tetrazole; triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1071/CH06357

Reference yield:

1D-1,4,5-tri-O-allyl-3,6-di-O-benzyl-myo-inositol (104873-74-7) → Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester (104846-25-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 81 percent / sodium hydride / dimethylformamide / 16 h / 20 °C

2: Huenig's base / [(Ph₃P)3RhCl] / ethanol; H₂O; toluene / 2 h / Heating

3: 117 mg / acetyl chloride / methanol; CH₂Cl₂ / 1.17 h / 20 °C

4: 1H-tetrazole / CH₂Cl₂ / 45 h

5: 291 mg / mCPBA / CH₂Cl₂ / -78 - 20 °C

6: triethylamine / CH₂Cl₂ / 16 h / 20 °C

With 1H-tetrazole; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1071/CH06357

Reference yield:

(-)-1D-1,4,5-tris-O-allyl-2,3,6-tris-O-benzyl-myo-inositol (104873-75-8) → Phosphoric acid mono-((1R,2R,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-phosphonooxy-cyclohexyl) ester (104846-25-5)

Guidance literature:

Multi-step reaction with 5 steps

1: Huenig's base / [(Ph₃P)3RhCl] / ethanol; H₂O; toluene / 2 h / Heating

2: 117 mg / acetyl chloride / methanol; CH₂Cl₂ / 1.17 h / 20 °C

3: 1H-tetrazole / CH₂Cl₂ / 45 h

4: 291 mg / mCPBA / CH₂Cl₂ / -78 - 20 °C

5: triethylamine / CH₂Cl₂ / 16 h / 20 °C

With 1H-tetrazole; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; Wilkinson's catalyst; In methanol; ethanol; dichloromethane; water; toluene;

DOI:10.1071/CH06357

upstream raw materials:

1D-2,3,6-Tri-O-benzyl-myo-inositol 1,4,5-tris

2,3,6-tris-O-(phenylmethyl)-D-myo-inositol

benzyl bromide

1D-1,4,5-tri-O-allyl-3,6-di-O-benzyl-myo-inositol

Downstream raw materials:

D-myo-inositol 1,4,5-triphosphate