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

Base Information

Chemical Name:(2R,3R,4R,5S)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine
CAS No.:340970-02-7
Molecular Formula:C₃₆H₄₃NO₄Si
Molecular Weight:581.827
Hs Code.:

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

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

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

There total 10 articles about (2R,3R,4R,5S)-3,4-dibenzyloxy-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:

: 340969-94-0
5-azido-3,4-di-O-benzyl-1-O-tert-butyldiphenylsilyl-5-deoxy-α-L-sorbopyranose

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

Guidance literature:: With hydrogen; nickel; In methanol; for 19h; under 2587.71 Torr;
DOI:10.1016/S0008-6215(00)00319-0

Reference yield:

: 100-39-0
benzyl bromide

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

Guidance literature:: Multi-step reaction with 6 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

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

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

Guidance literature:: Multi-step reaction with 5 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

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