4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

Base Information

Chemical Name:4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside
CAS No.:755008-19-6
Molecular Formula:C₄₃H₄₁N₃O₈
Molecular Weight:727.814
Hs Code.:

Synonyms:4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

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Chemical Property of 4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

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Technology Process of 4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

There total 6 articles about 4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside 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: 78.0%

: 755008-26-5
4-(tert-butyldiphenylsilyloxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glucopyranoside

: 755008-19-6
4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃;
DOI:10.1002/ejoc.200400111

Reference yield:

: 28920-43-6
(fluorenylmethoxy)carbonyl chloride

: 755008-19-6
4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / DMAP / pyridine / 2 h / 20 °C

2: 95 percent / HF*pyridine / tetrahydrofuran / 20 °C

3: 95 percent / NaH / CH₂Cl₂ / 0.5 h / 0 °C

4: 60 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / 20 °C

5: 78 percent / HF*pyridine / tetrahydrofuran / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.200400111

Reference yield:

: 174077-02-2
dimethylthexylsilyl 3,6-di-O-benzyl-2-deoxy-2-azido-β-D-glucopyranoside

: 755008-19-6
4-(hydroxymethyl)benzyl 2-azido-3,6-di-O-benzyl-2-deoxy-4-O-(9-fluorenylmethoxycarbonyl)-β-D-glycopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / DMAP / pyridine / 2 h / 20 °C

2: 95 percent / HF*pyridine / tetrahydrofuran / 20 °C

3: 95 percent / NaH / CH₂Cl₂ / 0.5 h / 0 °C

4: 60 percent / 4 Angstroem molecular sieves; TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / 20 °C

5: 78 percent / HF*pyridine / tetrahydrofuran / 20 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; sodium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; dichloromethane; acetonitrile;
DOI:10.1002/ejoc.200400111