3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

Base Information

• Chemical Name: 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol
• CAS No.: 294637-45-9
• Molecular Formula: C₃₀H₄₃BrO₅Si
• Molecular Weight: 591.658

Synonyms:3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

Chemical Property of 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

Chemical Property:

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Technology Process of 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

There total 3 articles about 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol 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: 72.0%

p-methoxybenzyl chloride (824-94-2) + 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-61-9) → 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-45-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1021/ja0008665

Reference yield:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) → 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO

1.2: 86 percent / TBAI

2.1: 72 percent / NaH / dimethylformamide; various solvent(s) / 0.5 h / 20 °C

With sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Etherification / 2.1: Etherification;

DOI:10.1021/ja0008665

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → 3-O-(4-bromobenzyl)-4-O-(4-methoxybenzyl)-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO

1.2: 86 percent / TBAI

2.1: 72 percent / NaH / dimethylformamide; various solvent(s) / 0.5 h / 20 °C

With sodium hydride; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Etherification / 2.1: Etherification;

DOI:10.1021/ja0008665

upstream raw materials:

p-methoxybenzyl chloride

1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

1-bromomethyl-4-bromobenzene

Downstream raw materials:

{4-[(2R,3S,4R)-3-(4-Methoxy-benzyloxy)-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yloxymethyl]-phenyl}-methyl-phenyl-amine

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