1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

Base Information

Chemical Name:1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose
CAS No.:1310019-05-6
Molecular Formula:C₂₁H₃₅NO₄Si
Molecular Weight:393.599
Hs Code.:

Synonyms:1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

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Chemical Property of 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

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Technology Process of 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

There total 4 articles about 1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose 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%

: 103931-45-9
5-O-(tert-butyldimethylsilyl)-1,2-O-isopropylidene-α-D-erythro-pentofuranos-3-ulose

: 100-46-9
benzylamine

: 1310019-05-6
1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

Guidance literature:: In 2,2,2-trifluoroethanol; at 37 ℃; for 0.166667h;
DOI:10.1016/j.tet.2012.12.049

Reference yield:

: 85951-12-8
1,2-O-isopropylidene-5-O-(tert-butyl)dimethylsilyl-α-D-xylofuranoside

: 1310019-05-6
1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 5 h / -78 °C

2.1: titanium tetrachloride / tetrahydrofuran / 0 °C

2.2: -30 °C

With oxalyl dichloride; titanium tetrachloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo200639t

Reference yield:

: 20031-21-4
1,2-O-isopropylidene-α-D-xylose

: 1310019-05-6
1,2-O-isopropylidene-5-O-(tert-butyldimethylsilyl)-3-deoxy-3-benzylamino-α-D-ribofuranose

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole / dichloromethane / 1 h / 20 °C

2: pyridinium dichromate; acetic anhydride / dichloromethane / 1 h / Reflux

3: 2,2,2-trifluoroethanol / 0.17 h / 37 °C

With 1H-imidazole; pyridinium dichromate; acetic anhydride; In dichloromethane; 2,2,2-trifluoroethanol;
DOI:10.1016/j.tet.2012.12.049