Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester

Base Information

• Chemical Name: Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester
• CAS No.: 864372-96-3
• Molecular Formula: C₄₈H₅₁O₁₈P₃
• Molecular Weight: 1008.84

Synonyms:Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester

Chemical Property of Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester

There total 4 articles about Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-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:

2,4,5-tris-O-acetyl-3,6-bis-O-(di-O-benzylphospho)-D-myo-inositol (864372-95-2) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester (864372-96-3)

Guidance literature:

2,4,5-tris-O-acetyl-3,6-bis-O-(di-O-benzylphospho)-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)-1,4-bis-O-(di-O-benzylphospho)conduritol B (222420-77-1) → Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester (864372-96-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 86 percent / pyridine / 12 h / 20 °C

2.1: 77 percent / NaIO₄; RuCl₃*3H₂O / acetonitrile; H₂O / 0.12 h / cooling

3.1: p-TSA*H₂O / tetrahydrofuran / 24 h / 20 °C

3.2: 83 percent / AcOH; water / 1.5 h / 20 °C

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

4.2: 570 mg / m-CPBA / CH₂Cl₂ / -40 - 20 °C

With pyridine; 1H-tetrazole; ruthenium trichloride; sodium periodate; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1002/ejoc.200400911

Reference yield:

4,5-di-O-acetyl-3,6-bis-O-(di-O-benzylphospho)-D-myo-inositol (864372-79-2) → Acetic acid (1R,2R,3S,4S,5R,6R)-3,4-diacetoxy-2,5-bis-(bis-benzyloxy-phosphoryloxy)-6-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-cyclohexyl ester (864372-96-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: p-TSA*H₂O / tetrahydrofuran / 24 h / 20 °C

1.2: 83 percent / AcOH; water / 1.5 h / 20 °C

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

2.2: 570 mg / m-CPBA / CH₂Cl₂ / -40 - 20 °C

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

DOI:10.1002/ejoc.200400911

upstream raw materials:

2,4,5-tris-O-acetyl-3,6-bis-O-(di-O-benzylphospho)-D-myo-inositol

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

(1S,2R,3R,4S)-1,4-bis-O-(di-O-benzylphospho)conduritol B

(1S,2R,3R,4S)-2,3-di-O-acetyl-1,4-bis-O-(di-O-benzylphospho)conduritol B

Downstream raw materials:

Inositol 1,3,4-triphosphate

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