(2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine

Base Information

• Chemical Name: (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine
• CAS No.: 1335000-88-8
• Molecular Formula: C₄₃H₄₉NO₃Si
• Molecular Weight: 655.952

Synonyms:(2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine

Chemical Property of (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine

There total 8 articles about (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine 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: 83.0%

(2R,3S,5S)-5-((tert-butyldiphenylsilyloxy)methyl)-2-(hydroxymethyl)pyrrolidin-3-ol (1335000-87-7) + benzyl bromide (100-39-0) → (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine (1335000-88-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 6h;

DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

(S,E)-tert-butyl-4-(4-ethoxy-4-oxobut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate (905718-71-0) → (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine (1335000-88-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: methanol / 1 h / 20 °C

1.2: 0.5 h

2.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

3.1: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; toluene; tert-butyl alcohol / 24 h / 0 °C

3.2: 0.75 h

4.1: triethylamine / dichloromethane / 72 h / 0 - 5 °C

5.1: dichloromethane / 2 h / 20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

7.1: sodium tetrahydroborate / ethanol / 3 h / 20 °C

8.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

With 1H-imidazole; methanol; sodium tetrahydroborate; osmium(VIII) oxide; methanesulfonamide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.1: Sharpless dihydroxylation;

DOI:10.1016/j.tetasy.2011.06.018

Reference yield:

5-tert-butoxycarbonylamino-6-hydroxy-hex-2-enoic acid ethyl ester → (2R,3S,5S)-1-benzyl-3-(benzyloxy)-2-(benzyloxymethyl)-5-((tert-butyldiphenylsilyloxy)methyl)pyrrolidine (1335000-88-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1H-imidazole / dichloromethane / 4 h / 0 °C

2.1: osmium(VIII) oxide; methanesulfonamide; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III) / water; toluene; tert-butyl alcohol / 24 h / 0 °C

2.2: 0.75 h

3.1: triethylamine / dichloromethane / 72 h / 0 - 5 °C

4.1: dichloromethane / 2 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C

6.1: sodium tetrahydroborate / ethanol / 3 h / 20 °C

7.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide / 6 h / 0 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; methanesulfonamide; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); In ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Sharpless dihydroxylation;

DOI:10.1016/j.tetasy.2011.06.018

upstream raw materials:

(S,E)-tert-butyl-4-(4-ethoxy-4-oxobut-2-enyl)-2,2-dimethyloxazolidine-3-carboxylate

(S,E)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)hex-2-enoate

(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyhexanoate

(2R,3S,5S)-ethyl 5-(tert-butoxycarbonylamino)-6-(tert-butyldiphenylsilyloxy)-3-hydroxy-2-(tosyloxy)hexanoate

Downstream raw materials:

C₂₇H₂₉NO₃

C₂₇H₂₉NO₄

((2S,4S,5R)-1-benzyl-4-(benzyloxy)-5-(benzyloxymethyl)pyrrolidin-2-yl)methanol

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