5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

Base Information

Chemical Name:5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose
CAS No.:1379002-82-0
Molecular Formula:C₂₇H₃₅NO₇Si
Molecular Weight:513.663
Hs Code.:

Synonyms:5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

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Chemical Property of 5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

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Technology Process of 5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

There total 4 articles about 5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose 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: 84.0%

: 1379002-57-9
3-amino-3-deoxy-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

: 2258-42-6
formyl acetic anhydride

: 1379002-82-0
5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

Guidance literature:: With sodium hydrogencarbonate; In dichloromethane; water; for 2.5h;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

: 172751-32-5
5-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-β-D-threo-pentofuranose-3-ulose

: 1379002-82-0
5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 4 steps

1: lithium hexamethyldisilazane / tetrahydrofuran / -78 °C

2: sodium azide; 18-crown-6 ether; 1,8-diazabicyclo[5.4.0]undec-7-ene / 50 °C

3: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr

4: sodium hydrogencarbonate / dichloromethane; water / 2.5 h

With sodium azide; 18-crown-6 ether; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; 2: modified Corey-Link reaction;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

: 352541-84-5
3-C-azido-5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

: 1379002-82-0
5-O-tert-butyldiphenylsilyl-3-deoxy-3-formamido-1,2-O-isopropylidene-3-C-methoxycarbonyl-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 2 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 0.5 h / 20 °C / 760.05 Torr

2: sodium hydrogencarbonate / dichloromethane; water / 2.5 h

With palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; In methanol; dichloromethane; water;
DOI:10.1016/j.tet.2012.03.087