methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS No.: 1256137-67-3
• Molecular Formula: C₂₂H₃₂N₂O₇Si
• Molecular Weight: 464.591

Synonyms:methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Chemical Property of methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

There total 4 articles about methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside 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:

C22H33BrO7Si (1256137-72-0) → methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (1256137-67-3)

Guidance literature:

With N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ja1054065

Reference yield:

methyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (1256137-62-8) → methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (1256137-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

2: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C / Inert atmosphere

With pyridine; N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1080/07328303.2011.614983

Reference yield:

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (71117-37-8) → methyl 4,6-O-benzylidene-2-O-diazoacetyl-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside (1256137-67-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

3: N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0 °C / Inert atmosphere

With pyridine; 1H-imidazole; N,N'-ditosylhydrazine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1080/07328303.2011.614983

upstream raw materials:

C₂₂H₃₃BrO₇Si

methyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside

tert-butyldimethylsilyl chloride

(2R,4aR,6R,7R,8R,8aS)-6-Methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

C₂₂H₃₂O₇Si

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