1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside

Base Information

• Chemical Name: 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside
• CAS No.: 1422376-17-7
• Molecular Formula: C₂₂H₃₇NO₅Si
• Molecular Weight: 423.625
• Mol file: 1422376-17-7.mol

Synonyms:1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside

Chemical Property of 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside

There total 8 articles about 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside 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:

C22H35NO5Si → 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside (1422376-17-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 0.166667h;

DOI:10.1016/j.tet.2012.12.049

Reference yield:

1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose (55174-92-0) → 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside (1422376-17-7)

Guidance literature:

Multi-step reaction with 5 steps

1: hydroxylamine hydrochloride; sodium hydrogencarbonate / ethanol / 3.5 h / Reflux

2: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C / Reflux

3: 1H-imidazole / dichloromethane / 1 h / 20 °C

4: titanium(IV) isopropylate / 1 h / 20 °C

5: sodium tetrahydroborate / methanol / 0.17 h

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; lithium aluminium tetrahydride; hydroxylamine hydrochloride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1016/j.tet.2012.12.049

Reference yield:

1,2-O-isopropylidene-5-O-trimethylacetyl-α-D-erythro-pent-3-ulofuranose oxime (55174-95-3) → 1,2-O-isopropylidene-3-(4-methoxy)benzylamino-3-deoxy-5-O-tert-butyldimethylsilyl-α-D-ribofuranoside (1422376-17-7)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 1.5 h / 0 °C / Reflux

2: 1H-imidazole / dichloromethane / 1 h / 20 °C

3: titanium(IV) isopropylate / 1 h / 20 °C

4: sodium tetrahydroborate / methanol / 0.17 h

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; lithium aluminium tetrahydride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2012.12.049

upstream raw materials:

1,2-O-isopropylidene-5-O-2,2-dimethylpropanoyl-α-D-erythro-pent-3-ulofuranose

1,2-O-isopropylidene-5-O-trimethylacetyl-α-D-erythro-pent-3-ulofuranose oxime

3-amino-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

D-xylofuranose