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

Base Information

• Chemical Name: 2-O-acetyl-1,4-di-O-benzyl-3,5,6-tris-O-(3-oxo-1,5-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol
• CAS No.: 864373-02-4
• Molecular Formula: C₄₆H₄₇O₁₆P₃
• Molecular Weight: 948.791

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

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

Chemical Property:

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

There total 5 articles about 2-O-acetyl-1,4-di-O-benzyl-3,5,6-tris-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:

2-O-acetyl-1,4-di-O-benzyl-D-myo-inositol (864373-01-3) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → 2-O-acetyl-1,4-di-O-benzyl-3,5,6-tris-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864373-02-4)

Guidance literature:

2-O-acetyl-1,4-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:

(-)-1D-1,4-di-O-benzyl-myo-inositol (221555-39-1) → 2-O-acetyl-1,4-di-O-benzyl-3,5,6-tris-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864373-02-4)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: AcOH; water / 1 h / 20 °C

2.1: 1H-tetrazole / CH₂Cl₂ / 12 h / 20 °C

2.2: m-CPBA / CH₂Cl₂ / -40 - 20 °C

With 1H-tetrazole; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ejoc.200400911

Reference yield:

(+/-)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene (112212-81-4,145047-66-1) → 2-O-acetyl-1,4-di-O-benzyl-3,5,6-tris-O-(3-oxo-1,5-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)-D-myo-inositol (864373-02-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pig pancrease lipase type II / diethyl ether; aq. phosphate buffer / pH 7.0

2.1: 70 percent / NaOBn / tetrahydrofuran

3.1: NaIO₄; RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / cooling

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

4.2: AcOH; water / 1 h / 20 °C

5.1: 1H-tetrazole / CH₂Cl₂ / 12 h / 20 °C

5.2: m-CPBA / CH₂Cl₂ / -40 - 20 °C

With 1H-tetrazole; ruthenium trichloride; sodium periodate; pig pancrease lipase type II; toluene-4-sulfonic acid; sodium phenyl-methanolate; In tetrahydrofuran; phosphate buffer; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200400911

upstream raw materials:

2-O-acetyl-1,4-di-O-benzyl-D-myo-inositol

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

(-)-1D-1,4-di-O-benzyl-myo-inositol

(+/-)-(1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene

Downstream raw materials:

myo-inositol 1,4,5-trisphosphate

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