5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

Base Information

Chemical Name:5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose
CAS No.:1379002-86-4
Molecular Formula:C₃₄H₃₉N₃O₆Si
Molecular Weight:613.786
Hs Code.:

Synonyms:5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

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Chemical Property of 5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

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Technology Process of 5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

There total 3 articles about 5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-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: 62.0%

: 536-74-3
phenylacetylene

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

: 1379002-86-4
5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

Guidance literature:: With copper(II) sulfate; sodium L-ascorbate; In water; acetone; at 20 ℃; for 48h;
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

: 1379002-86-4
5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 3 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: copper(II) sulfate; sodium L-ascorbate / water; acetone / 48 h / 20 °C

With sodium azide; 18-crown-6 ether; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium L-ascorbate; lithium hexamethyldisilazane; In tetrahydrofuran; water; acetone; 2: modified Corey-Link reaction;
DOI:10.1016/j.tet.2012.03.087

Reference yield:

: 352541-83-4
5-O-tert-butyldiphenylsilyl-3-C-trichloromethyl-1,2-O-isopropylidene-β-D-lyxofuranose

: 1379002-86-4
5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-3-C-methoxycarbonyl-3-(4-phenyl-1H-1,2,3-triazol-1-yl)-β-D-arabinofuranose

Guidance literature:: Multi-step reaction with 2 steps

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

2: copper(II) sulfate; sodium L-ascorbate / water; acetone / 48 h / 20 °C

With sodium azide; 18-crown-6 ether; copper(II) sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium L-ascorbate; In water; acetone; 1: modified Corey-Link reaction;
DOI:10.1016/j.tet.2012.03.087