((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

Base Information

• Chemical Name: ((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane
• CAS No.: 364635-35-8
• Molecular Formula: C₁₉H₂₉N₃O₅Si
• Molecular Weight: 407.542
• Mol file: 364635-35-8.mol

Synonyms:((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

Chemical Property of ((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane

There total 1 articles about ((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane 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: 85.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + 3-O-Benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose (85458-76-0) → ((3aR,6S,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane + ((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane (364635-35-8)

Guidance literature:

3-O-Benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose; With trimethylsilylazide; 4 A molecular sieve; In acetonitrile; at 0 ℃; for 0.0833333h;

trimethylsilyl trifluoromethanesulfonate; at 0 ℃; for 0.0833333h;

DOI:10.1016/S0957-4166(01)00223-3

Reference yield:

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane (364635-35-8) → (3aR,6R,7S,7aR)-7-Benzyloxy-2,2-dimethyl-6-trimethylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylamine (364635-36-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0957-4166(01)00223-3

Reference yield:

((3aR,6R,7S,7aR)-6-Azido-7-benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy)-trimethyl-silane (364635-35-8) → methyl (3-O-benzyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl amine)onate

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / tetrabutyl ammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

2: 92 percent / oxalyl chloride; dimethylsulfoxide; triethylamine / CH₂Cl₂ / 0.08 h / -70 °C

3: NaClO₂; NaH₂PO₄*2H₂O; 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O / 0 °C

4: 0.089 g / diethyl ether; methanol / 0.33 h / 0 °C

5: hydrogen / palladium on carbon / methanol / 1 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; 2: Swern oxidation;

DOI:10.1016/j.tet.2005.09.128

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

3-O-Benzyl-1,2:4,5-di-O-isopropylidene-β-D-fructopyranose

Downstream raw materials:

(3aR,6R,7S,7aR)-7-Benzyloxy-2,2-dimethyl-6-trimethylsilanyloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylamine

2-azido-3-O-benzyl-1-dehydro-2-deoxy-4,5-O-isopropylidene-β-D-fructopyranose

methyl (3-O-benzyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ulopyranosyl azide)onate

methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate