dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate

Base Information

• Chemical Name: dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate
• CAS No.: 1264709-49-0
• Molecular Formula: C₅₆H₅₆O₁₁P₂
• Molecular Weight: 967.002

Synonyms:dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate

Chemical Property of dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate

There total 6 articles about dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate 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: 66.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + 1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol (105017-77-4) → dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate (1264709-49-0)

Guidance literature:

Dibenzyl N,N-diisopropylphosphoramidite; 1D-(1,2,4/3)-2,3,4-Tri-O-benzyl-5-C-(hydroxymethyl)-5-cyclohexen-1,2,3,4-tetrol; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 4.66667h; Inert atmosphere;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1039/c0ob00475h

Reference yield:

C39H46O4S2 (851542-23-9) → dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate (1264709-49-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; mercury dichloride; mercury(II) oxide / acetonitrile / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / Reflux; Inert atmosphere

3.1: acetic anhydride; zinc(II) chloride / acetic acid / 2 h / 20 °C / Inert atmosphere

3.2: 4 h / 20 °C / Inert atmosphere

4.1: 1H-tetrazole / dichloromethane / 4.67 h / 20 °C / Inert atmosphere

4.2: -78 - 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 1H-tetrazole; water; acetic anhydride; mercury dichloride; mercury(II) oxide; zinc(II) chloride; In dichloromethane; acetic acid; acetonitrile;

DOI:10.1039/c0ob00475h

Reference yield:

(1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol (213400-35-2) → dibenzyl (1S,4R,5S,6R)-4,5,6-tris(benzyloxy)-3-(([bis(benzoxy)phosphoryl]oxy)methyl)cyclohex-2-en-1-yl phosphate (1264709-49-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic anhydride; zinc(II) chloride / acetic acid / 2 h / 20 °C / Inert atmosphere

1.2: 4 h / 20 °C / Inert atmosphere

2.1: 1H-tetrazole / dichloromethane / 4.67 h / 20 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With 1H-tetrazole; acetic anhydride; zinc(II) chloride; In dichloromethane; acetic acid;

DOI:10.1039/c0ob00475h

upstream raw materials:

(2R,3S,4R)-2,3,4-tris(benzyloxy)-5-(benzyloxymethyl)hex-5-enal

C₃₉H₄₆O₄S₂

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

Dibenzyl N,N-diisopropylphosphoramidite

Downstream raw materials:

valienol 1,7-diphosphate

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