3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone

Base Information

• Chemical Name: 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone
• CAS No.: 1247813-76-8
• Molecular Formula: C₂₉H₄₂O₅Si
• Molecular Weight: 498.735
• Mol file: 1247813-76-8.mol

Synonyms:3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone

Chemical Property of 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone

There total 4 articles about 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone 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: 44.0%

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (196703-95-4) → 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone (1247813-76-8)

Guidance literature:

With pyridinium chlorochromate; In 1,2-dichloro-ethane; at 80 ℃; for 6h; Inert atmosphere; Molecular sieve;

DOI:10.1039/c0cc00586j

Reference yield:

D-glucal triacetate (2873-29-2) → 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone (1247813-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate; methanol / 20 °C

1.2: 20 °C

1.3: 20 °C

2.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere

With methanol; sodium methylate; pyridinium chlorochromate; In 1,2-dichloro-ethane;

DOI:10.1002/chem.201402149

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → 3,4-di-O-benzyl-6-O-triisopropylsilyl-2-deoxy-D-arabino-hexono-1,5-lactone (1247813-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate; methanol / 20 °C

1.2: 20 °C

1.3: 20 °C

2.1: pyridinium chlorochromate / 1,2-dichloro-ethane / 6 h / 80 °C / Inert atmosphere

With methanol; sodium methylate; pyridinium chlorochromate; In 1,2-dichloro-ethane;

DOI:10.1002/chem.201402149

upstream raw materials:

1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

D-glucal triacetate

triisopropylsilyl trifluoromethanesulfonate

benzyl bromide

Downstream raw materials:

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-methoxybenzyl-D-glucal

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-methylbenzyl-D-glucal

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-(2-naphthylmethyl)-D-glucal

1-(2-phenyl-ethynyl)-3,4-di-O-benzyl-6-O-p-fluorobenzyl-D-glucal