(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Base Information

Chemical Name:(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
CAS No.:927809-69-6
Molecular Formula:C₄₄H₄₇NO₇Si
Molecular Weight:729.945
Hs Code.:

Synonyms:(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

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Chemical Property of (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

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Technology Process of (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

There total 8 articles about (2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)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: 47.0%

: (3R,4R,5R)-4-benzoyloxy-3-benzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 501-53-1,94274-21-2
benzyl chloroformate

: 927809-69-6
(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 927809-70-9
(2S,3R,4R,5R)-4-(benzoyloxy)-3-(benzyloxy)-1-(benzyloxycarbonyl)-2-[(tert-butyldiphenylsilyloxy)methyl]-5-(hydroxymethyl)pyrrolidine

Guidance literature:: With potassium carbonate; In acetone; at 20 ℃;
DOI:10.1016/j.tet.2006.11.070

Reference yield:

: 98-88-4
benzoyl chloride

: 927809-69-6
(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 57 percent / TEA / dioxane / 4 h / 20 °C

2: 82 percent / iodine; triphenylphosphine; imidazole / toluene / 2 h / 110 °C

3: 56 percent / lithium azide / dimethylformamide / 24 h / 100 °C

4: 80 percent / aq. TFA / 2 h / 20 °C

5: 78 percent / imidazole / dimethylformamide / 72 h / 20 °C

6: hydrogen / Raney nickel / methanol / 24 h / 3620.04 Torr

7: 47 percent / potassium carbonate / acetone / 20 °C

With 1H-imidazole; lithium azide; TEA; hydrogen; iodine; potassium carbonate; triphenylphosphine; trifluoroacetic acid; 1H-imidazole; nickel; In 1,4-dioxane; methanol; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.tet.2006.11.070

Reference yield:

: 927809-67-4
5-azido-4-O-benzoyl-3-O-benzyl-5-deoxy-β-D-fructopyranose

: 927809-69-6
(2R,3R,4R,5R)-4-benzoyloxy-3-benzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / imidazole / dimethylformamide / 72 h / 20 °C

2: hydrogen / Raney nickel / methanol / 24 h / 3620.04 Torr

3: 47 percent / potassium carbonate / acetone / 20 °C

With hydrogen; potassium carbonate; 1H-imidazole; nickel; In methanol; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.tet.2006.11.070