1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

Base Information

• Chemical Name: 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose
• CAS No.: 110046-81-6
• Molecular Formula: C₂₂H₃₂O₅Si
• Molecular Weight: 404.579

Synonyms:1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

Chemical Property of 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

Chemical Property:

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Technology Process of 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose

There total 3 articles about 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose 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: 99.1%

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) + 3-(tert-butyldimethylsiloxy)propynyldiethylalane (89731-32-8) → 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose (110046-81-6)

Guidance literature:

In toluene; at 80 ℃; for 0.75h;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose (110046-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h / Ambient temperature

2: 1.) n-BuLi, 2.) Et₂AlCl

With dmap; n-butyllithium; diethylaluminium chloride; triethylamine; In dichloromethane;

DOI:10.1021/jo00229a013

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) + tert-Butyldimethyl(prop-2-ynyloxy)silane (76782-82-6) → 1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-tert-butyldimethylsilyloxyprop-1-ynyl)-β-D-glucopyranose (110046-81-6)

Guidance literature:

With n-butyllithium; diethylaluminium chloride; Yield given. Multistep reaction;

DOI:10.1021/jo00229a013

upstream raw materials:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

tert-Butyldimethyl(prop-2-ynyloxy)silane

3-(tert-butyldimethylsiloxy)propynyldiethylalane

tert-butyldimethylsilyl chloride

Downstream raw materials:

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(3-hydroxypropynyl)-β-D-glucopyranose

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