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

Base Information

Chemical Name:(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
CAS No.:340970-04-9
Molecular Formula:C₄₄H₄₉NO₆Si
Molecular Weight:715.962
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 11 articles about (2R,3R,4R,5S)-3,4-dibenzyloxy-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: 68.0%

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

: 340970-02-7
(2R,3R,4R,5S)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 340970-04-9
(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Guidance literature:: With triethylamine; In methanol; at 20 ℃; for 2h;
DOI:10.1016/S0008-6215(00)00319-0

Reference yield:

: 100-39-0
benzyl bromide

: 340970-04-9
(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1.1: dibuthyltin oxide / methanol / 2 h / Heating

1.2: 55 percent / dimethylformamide / 4 h / 110 °C

2.1: 74 percent / Et₃N / CH₂Cl₂ / 20 °C

3.1: 98 percent / NaN₃ / dimethylformamide / 48 h / 100 °C

4.1: 78.4 percent / TFA / H₂O / 24 h / 20 °C

5.1: 100 percent / imidazole / dimethylformamide / 20 h / 20 °C

6.1: H₂ / Raney nickel / methanol / 19 h / 2587.71 Torr

7.1: 68 percent / Et₃N / methanol / 2 h / 20 °C

With 1H-imidazole; sodium azide; hydrogen; di(n-butyl)tin oxide; triethylamine; trifluoroacetic acid; nickel; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)00319-0

Reference yield:

: 340969-76-8
3,4-di-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose

: 340970-04-9
(2R,3R,4R,5S)-3,4-dibenzyloxy-N-benzyloxycarbonyl-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / Et₃N / CH₂Cl₂ / 20 °C

2: 98 percent / NaN₃ / dimethylformamide / 48 h / 100 °C

3: 78.4 percent / TFA / H₂O / 24 h / 20 °C

4: 100 percent / imidazole / dimethylformamide / 20 h / 20 °C

5: H₂ / Raney nickel / methanol / 19 h / 2587.71 Torr

6: 68 percent / Et₃N / methanol / 2 h / 20 °C

With 1H-imidazole; sodium azide; hydrogen; triethylamine; trifluoroacetic acid; nickel; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)00319-0