(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine

Base Information

Chemical Name:(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine
CAS No.:883743-24-6
Molecular Formula:C₂₅H₃₃NO₅
Molecular Weight:427.541
Hs Code.:

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

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

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

There total 8 articles about (2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine 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: 53.0%

: 883743-23-5
5-azido-3,4-di-O-benzyl-5-deoxy-1-O-pivaloyl-α-L-tagatopyranose

: 883743-24-6
(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine

Guidance literature:: With hydrogen; nickel; In methanol; for 5h; under 3102.89 Torr;
DOI:10.1016/j.tet.2005.12.023

Reference yield:

: 883743-20-2
5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-α-L-tagatopyranose

: 883743-24-6
(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / NaH / dimethylformamide / 0.25 h / 20 °C

2: 78 percent / aq. TFA / 24 h / 20 °C

3: 88 percent / Et₃N / CH₂Cl₂ / 5 h / 20 °C

4: 53 percent / H₂; Raney Ni / methanol / 5 h / 3102.89 Torr

With hydrogen; nickel; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2005.12.023

Reference yield:

: 883743-18-8
Methanesulfonic acid (5S,8R,9R)-9-benzyloxy-2,2-dimethyl-10-oxo-1,3,6-trioxa-spiro[4.5]dec-8-yl ester

: 883743-24-6
(2R,3S,4R,5S)-3,4-dibenzyloxy-2,5-bis(hydroxymethyl)-2'-O-pivaloylpyrrolidine

Guidance literature:: Multi-step reaction with 6 steps

1: 76 percent / NaBH₄ / methanol / 0 °C

2: 82 percent / LiN₃ / dimethylformamide / 2 h / 100 °C

3: 85 percent / NaH / dimethylformamide / 0.25 h / 20 °C

4: 78 percent / aq. TFA / 24 h / 20 °C

5: 88 percent / Et₃N / CH₂Cl₂ / 5 h / 20 °C

6: 53 percent / H₂; Raney Ni / methanol / 5 h / 3102.89 Torr

With sodium tetrahydroborate; lithium azide; hydrogen; nickel; sodium hydride; triethylamine; trifluoroacetic acid; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2005.12.023