(3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

Base Information

• Chemical Name: (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole
• CAS No.: 162792-19-0
• Molecular Formula: C₃₀H₃₄O₅
• Molecular Weight: 474.597
• Mol file: 162792-19-0.mol

Synonyms:(3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

Chemical Property of (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole

There total 3 articles about (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 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: 99.0%

benzyl bromide (100-39-0) + 1D-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol (148888-40-8) → (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (162792-19-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jm00007a001

Reference yield: 74.0%

benzyl bromide (100-39-0) + (3aS,4R,5S,6R,7aR)-2,2-Dimethyl-hexahydro-benzo[1,3]dioxole-4,5,6-triol → (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (162792-19-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; 1.) 0 deg C, 2 h, 2.) room temp., 5.5 h;

DOI:10.1016/S0040-4020(97)10003-5

Reference yield:

1D-5,6-di-O-benzoyl-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol (132662-66-9) → (3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (162792-19-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / K₂CO₃ / methanol

2: 99 percent / NaH / dimethylformamide

With sodium hydride; potassium carbonate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00007a001

upstream raw materials:

benzyl bromide

1D-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol

1D-5,6-di-O-benzoyl-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol

Downstream raw materials:

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyloxy)-phosphanyloxy]-1-hexadecanoyloxymethyl-ethyl ester

Benzoic acid (1R,2R,3S,4R,6R)-2,3,4-tris-benzyloxy-6-phenoxythiocarbonyloxy-cyclohexyl ester

Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R)-2,3,4-tris-benzyloxy-cyclohexyl ester