(1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol

Base Information

• Chemical Name: (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol
• CAS No.: 281681-94-5
• Molecular Formula: C₂₄H₄₃NO₄Si₂
• Molecular Weight: 465.781
• Mol file: 281681-94-5.mol

Synonyms:(1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol

Chemical Property of (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol

There total 2 articles about (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol 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: 64.0%

(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)-α-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazine-2-methanol methanesulfonate → (R)-(-)-2,2-diphenylcyclopentanol (126421-67-8) + (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol (281681-94-5)

Guidance literature:

(2R,3R,3aR,4S,5R,6S)-4,5-bis(benzoyloxy)-3-(dimethylphenylsilyl)-α-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-6-[[(1R)-2,2-diphenylcyclopentyl]oxy]isoxazolo[2,3-b][1,2]-2-oxazine-2-methanol methanesulfonate; With hydrogen; nickel; In methanol; at 20 ℃; for 42h; under 13446.2 Torr;

With potassium carbonate; In methanol; at 20 ℃; for 4h; Further stages.;

DOI:10.1021/jo991680v

Reference yield: 64.0%

C56H69NSi2O11S → (1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol (281681-94-5)

Guidance literature:

C₅₆H₆₉NSi₂O₁₁S; With hydrogen; nickel; In methanol; under 13446.2 Torr;

With potassium carbonate; In methanol; Further stages.;

DOI:10.1021/ol9909886

Reference yield: 84.0%

(1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol (281681-94-5) → casuarine (159440-57-0)

Guidance literature:

(1S,2S,5R,6R,7R,7aR)-7-(dimethylphenylsilyl)-5-[[[dimethyl(1,1,2-trimethylpropyl)silyl]oxy]methyl]hexahydro-1H-pyrrolizine-1,2,6-triol; With mercury(II) trifluoroacetate; In chloroform; acetic acid; trifluoroacetic acid; at 20 ℃; for 1h;

With peracetic acid; In acetic acid; at 20 ℃; for 18h; Further stages.;

DOI:10.1021/jo991680v

Downstream raw materials:

casuarine

Refernces

• 1、 Denmark, Scott E.,Hurd, Alexander R.. "Synthesis of (+)-Casuarine". . p. 2875 - 2886. Retrieved 2007/10/03.