methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside
CAS No.:473542-37-9
Molecular Formula:C₂₈H₃₇N₃O₇Si
Molecular Weight:555.703
Hs Code.:

Synonyms:methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

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Technology Process of methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

There total 5 articles about methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-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: 72.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 473542-36-8
methyl 2-azido-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

: 473542-37-9
methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 18h;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W

Reference yield:

: 87038-18-4
methyl 2-acetylamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 473542-37-9
methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 3.28 g / Ba(OH)2*8H₂O / H₂O; methanol / 18 h / 100 °C

2: 73 percent / TfN₃; 4-(dimethylamino)pyridine / methanol / 18 h / 20 °C

3: 99 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / pyridine / 18 h / 20 °C

4: 81 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

5: 72 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; dmap; barium dihydroxide; triflic azide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W

Reference yield:

: 99745-44-5
Methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside

: 473542-37-9
methyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-levulinoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / TfN₃; 4-(dimethylamino)pyridine / methanol / 18 h / 20 °C

2: 99 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / pyridine / 18 h / 20 °C

3: 81 percent / trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

4: 72 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; dmap; triflic azide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/1099-0690(200207)2002:13<2033::AID-EJOC2033>3.0.CO;2-W