phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside
• CAS No.: 913060-93-2
• Molecular Formula: C₄₁H₃₄O₈S
• Molecular Weight: 686.782

Synonyms:phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside

Chemical Property:

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Technology Process of phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside

There total 3 articles about phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside 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: 85.0%

phenyl 4,6-O-benzylidene-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside (913061-12-8) + benzyl chloride (100-44-7) → phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside (913060-93-2)

Guidance literature:

With pyridine; In dichloromethane; at 4 ℃; for 18h;

DOI:10.1021/ja0629817

Reference yield: 70.0%

phenyl 4,6-O-benzylidene-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside (913061-12-8) + benzoyl chloride (98-88-4) → phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside (913060-93-2)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.0c02935

Reference yield:

(fluorenylmethoxy)carbonyl chloride (28920-43-6) → phenyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenemethoxycarbonyl)-1-thio-β-D-galactopyranoside (913060-93-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; dimethyltin dichloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

With pyridine; dimethyltin dichloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/acs.joc.0c02935

upstream raw materials:

phenyl 4,6-O-benzylidene-3-O-(9-fluorenylmethoxycarbonyl)-1-thio-β-D-galactopyranoside

benzyl chloride

benzoyl chloride

(fluorenylmethoxy)carbonyl chloride

Downstream raw materials:

3-azidopropyl 2-O-benzoyl-4-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside

3-azidopropyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenylmethoxycarbonyl)-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside

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