Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

Base Information

• Chemical Name: Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester
• CAS No.: 162991-36-8
• Molecular Formula: C₆₉H₆₉O₁₂P₃
• Molecular Weight: 1183.22
• Mol file: 162991-36-8.mol

Synonyms:

Chemical Property of Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester

There total 4 articles about Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-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:

(±)-1,3,6-tri-O-benzyl-myo-inositol (98906-30-0,104873-76-9,111466-07-0,114297-88-0,114297-91-5,114419-08-8,115184-71-9,115509-76-7,118354-54-4,118354-55-5,128163-34-8,129706-80-5,136521-84-1,149713-88-2,149713-95-1,115509-75-6) + Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) → Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (162991-36-8)

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(02)00289-6

Reference yield:

benzyl bromide (100-39-0) → Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (162991-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dibutyltin oxide / toluene / 2.5 h / Heating

1.2: 85 percent / CsF / dimethylformamide / 20 °C

2.1: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1016/S0008-6215(02)00289-6

Reference yield:

D-3,6-di-O-benzyl-4,5-bis-O-(p-methoxybenzyl)-myo-inositol (111465-38-4) → Phosphorous acid dibenzyl ester (1S,2S,3S,4R,5R,6S)-2,3,6-tris-benzyloxy-4,5-bis-(bis-benzyloxy-phosphanyloxy)-cyclohexyl ester (162991-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dibutyltin oxide / toluene / 2.5 h / Heating

1.2: 85 percent / CsF / dimethylformamide / 20 °C

2.1: 85 percent / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 1H-tetrazole / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-tetrazole; di(n-butyl)tin oxide; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1016/S0008-6215(02)00289-6

upstream raw materials:

(±)-1,3,6-tri-O-benzyl-myo-inositol

Dibenzyl N,N-diisopropylphosphoramidite

benzyl bromide

D-3,6-di-O-benzyl-4,5-bis-O-(p-methoxybenzyl)-myo-inositol

Downstream raw materials:

D-1,3,6-tri-O-benzyl-2,4,5-tris-O-[di(benzyloxy)thiophosphoryl]-myo-inositol