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

Base Information

• Chemical Name: 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol
• CAS No.: 294637-61-9
• Molecular Formula: C₂₂H₃₅BrO₄Si
• Molecular Weight: 471.507

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

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

Chemical Property:

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

There total 1 articles about 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-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: 86.0%

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (137915-37-8) + 1-bromomethyl-4-bromobenzene (589-15-1) → 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-61-9)

Guidance literature:

1,2-dideoxy-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose; With di(n-butyl)tin oxide;

1-bromomethyl-4-bromobenzene; With tetra-(n-butyl)ammonium iodide; Further stages.;

DOI:10.1021/ja0008665

Reference yield: 93.0%

benzyl bromide (100-39-0) + 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-61-9) → 1,5-anhydro-4-O-benzyl-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (429679-57-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200203)2002:5<826::AID-EJOC826>3.0.CO;2-2

Reference yield: 80.0%

4-chlorobenzyl bromide (622-95-7) + 1,5-anhydro-3-O-(4-bromobenzyl)-2-deoxy-6-O-triisopropylsilyl-D-arabino-hex-1-enitol (294637-61-9) → [(2R,3S,4R)-4-(4-Bromo-benzyloxy)-3-(4-chloro-benzyloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-triisopropyl-silane (294637-62-0)

Guidance literature:

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

DOI:10.1021/ja0008665

upstream raw materials:

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

1-bromomethyl-4-bromobenzene

Downstream raw materials:

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

[(2R,3S,4R)-4-(4-Bromo-benzyloxy)-3-(4-chloro-benzyloxy)-3,4-dihydro-2H-pyran-2-ylmethoxy]-triisopropyl-silane

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

4-pentenyl 2,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannopyranoside

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