1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose

Base Information

• Chemical Name: 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose
• CAS No.: 240402-08-8
• Molecular Formula: C₁₉H₃₀O₄Si
• Molecular Weight: 350.53
• Mol file: 240402-08-8.mol

Synonyms:1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose

Chemical Property of 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose

There total 2 articles about 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose 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: 84.0%

benzyl bromide (100-39-0) + 1,4-anhydro-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose (240402-07-7) → 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose (240402-08-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00480-9

Reference yield:

1,4-anhydro-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-iodo-β-D-galactopyranose (161254-79-1) → 1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose (240402-08-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / Bu₃SnH; AIBN / benzene / 1 h / Heating

2: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 2 h / 0 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene; 1: Reduction / 2: Alkylation;

DOI:10.1016/S0040-4020(99)00480-9

Reference yield: 61.0%

1,4-anhydro-3-O-benzyl-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose (240402-08-8) + allyl-trimethyl-silane (762-72-1) → 4,7-anhydro-6-O-benzyl-1,2,3,5-tetradeoxy-D-galacto-non-1-enitol

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In various solvent(s); at -93 - -10 ℃;

DOI:10.1016/S0040-4020(99)00480-9

upstream raw materials:

benzyl bromide

1,4-anhydro-6-O-tert-butyldimethylsilyl-2-deoxy-β-D-lyxo-hexopyranose

1,4-anhydro-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-iodo-β-D-galactopyranose