(1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B

Base Information

• Chemical Name: (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B
• CAS No.: 864951-19-9
• Molecular Formula: C₃₇H₃₇O₁₃P₃
• Molecular Weight: 782.614

Synonyms:(1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B

Chemical Property of (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Technology Process of (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B

There total 4 articles about (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ⁵-2,4,3-benzodioxaphosphepin-3-yl)conduritol B 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:

(1R,2S,3S,4R)-1-O-benzylconduritol B (864951-03-1) + N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine (82372-35-8) → (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)conduritol B (864951-19-9)

Guidance literature:

(1R,2S,3S,4R)-1-O-benzylconduritol B; N,N-diethyl-1,5-dihydro-3H-2,4,3-benzodioxaphosphepin-3-amine; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 4h;

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

DOI:10.1002/ejoc.200400918

Reference yield:

(1S,2R,3S,6R)-6-benzyloxy-2-bromocyclohex-4-ene-1,3-diol (864950-99-2) → (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)conduritol B (864951-19-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LiOH / diethyl ether; methanol / 3 h / 10 °C

1.2: p-toluenesulfonic acid; water / tetrahydrofuran / 72 h / 20 °C

2.1: 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

2.2: m-CPBA / CH₂Cl₂ / -20 - 20 °C

With 1H-tetrazole; lithium hydroxide; In methanol; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200400918

Reference yield:

(1S,2R,3S,6S)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol (80582-73-6) → (1R,2S,3S,4R)-1-O-benzyl-2,3,4-tris-O-(3-oxo-1,4-dihydro-3λ5-2,4,3-benzodioxaphosphepin-3-yl)conduritol B (864951-19-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂SO₄ / CH₂Cl₂ / 72 h / 20 °C

2.1: LiOH / diethyl ether; methanol / 3 h / 10 °C

2.2: p-toluenesulfonic acid; water / tetrahydrofuran / 72 h / 20 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

3.2: m-CPBA / CH₂Cl₂ / -20 - 20 °C

With 1H-tetrazole; lithium hydroxide; sulfuric acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1002/ejoc.200400918

upstream raw materials:

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

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

(1S,2R,3S,6R)-6-benzyloxy-2-bromocyclohex-4-ene-1,3-diol

(1S,2R,3S,6S)-2-bromo-7-oxabicyclo[4.1.0]hept-4-en-3-ol

Downstream raw materials:

myo-Inositol 1,5,6-trisphosphate

myo-inositol 4,5,6-trisphosphate

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