1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol

Base Information

• Chemical Name: 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol
• CAS No.: 864372-89-4
• Molecular Formula: C₃₄H₃₇O₁₂P
• Molecular Weight: 668.634

Synonyms:1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol

Chemical Property of 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol

Chemical Property:

Purity/Quality:

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Technology Process of 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol

There total 5 articles about 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol 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: 60.0%

1,4,5-tri-O-acetyl-3,6-di-O-benzyl-D-myo-inositol (864372-88-3) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864372-89-4)

Guidance literature:

1,4,5-tri-O-acetyl-3,6-di-O-benzyl-D-myo-inositol; N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 12h;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -40 - 20 ℃;

DOI:10.1002/ejoc.200400911

Reference yield:

(1S,2R,3R,4S)-2,3-di-O-acetyl-1,4-di-O-benzylconduritol B (864372-74-7) → 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864372-89-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 87 percent / NaIO₄; RuCl₃*3H₂O / acetonitrile; ethyl acetate; H₂O / 0.17 h / cooling

2.1: p-TSA*H₂O / tetrahydrofuran / 24 h

2.2: 85 percent / AcOH; water / 1 h / 20 °C

3.1: 100 percent / TMS-OTf; 3 A MS / diethyl ether / 48 h / 20 °C

4.1: 1H-tetrazole / CH₂Cl₂ / 12 h / 20 °C

4.2: 60 percent / m-CPBA / CH₂Cl₂ / -40 - 20 °C

With 1H-tetrazole; ruthenium trichloride; sodium periodate; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;

DOI:10.1002/ejoc.200400911

Reference yield:

4,5-di-O-acetyl-3,6-di-O-benzyl-D-myo-inositol (864372-76-9) → 1,4,5-tri-O-acetyl-3,6-di-O-benzyl-2-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864372-89-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: p-TSA*H₂O / tetrahydrofuran / 24 h

1.2: 85 percent / AcOH; water / 1 h / 20 °C

2.1: 100 percent / TMS-OTf; 3 A MS / diethyl ether / 48 h / 20 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 12 h / 20 °C

3.2: 60 percent / m-CPBA / CH₂Cl₂ / -40 - 20 °C

With 1H-tetrazole; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200400911

upstream raw materials:

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

N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine

(1S,2R,3R,4S)-2,3-di-O-acetyl-1,4-di-O-benzylconduritol B

4,5-di-O-acetyl-3,6-di-O-benzyl-D-myo-inositol

Downstream raw materials:

myo-Inositol 2-phosphate

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