(2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

Base Information

• Chemical Name: (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine
• CAS No.: 872345-52-3
• Molecular Formula: C₅₂H₆₁NO₄Si₂
• Molecular Weight: 820.232

Synonyms:(2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

Chemical Property of (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

Chemical Property:

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Technology Process of (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrrolidine

There total 9 articles about (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-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: 73.0%

5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose (872345-48-7) → (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrrolidine (872345-52-3)

Guidance literature:

With hydrogen; nickel; In tetrahydrofuran; methanol; for 5h; under 3102.89 Torr;

DOI:10.1016/j.tet.2005.09.043

Reference yield: 43.0%

(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrroline (872345-50-1) → (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrrolidine (872345-52-3) + (2R,3R,4S,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrrolidine

Guidance literature:

With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; for 0.25h; cooling;

DOI:10.1016/j.tet.2005.09.043

Reference yield:

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one (872345-44-3) → (2R,3R,4S,5S)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ2-pyrrolidine (872345-52-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 88 percent / NaBH₄ / methanol / 1 h / cooling

2.1: 72 percent / NaH / dimethylformamide / 2 h / 20 °C

3.1: aq. TFA / 2 h / 20 °C

3.2: 2.31 g / imidazole / dimethylformamide / 20 h / 20 °C

4.1: 97 percent / PPh₃ / tetrahydrofuran / 5 h / Heating

5.1: 23 percent / AcOH; NaCNBH₃ / tetrahydrofuran / 0.25 h / cooling

With sodium tetrahydroborate; sodium hydride; sodium cyanoborohydride; acetic acid; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 4.1: Staudinger/aza-Wittig reaction;

DOI:10.1016/j.tet.2005.09.043

upstream raw materials:

(3S,4R,5R)-3,4-dibenzyloxy-2',5'-di-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)-δ²-pyrroline

5-azido-3,4-di-O-benzyl-1,6-di-O-tert-butyldiphenylsilyl-5-deoxy-D-psicose

(5S,8R,9R)-8-Azido-9-benzyloxy-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]decan-10-one

5-azido-4-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-D-psicopyranose

Downstream raw materials:

(2R,3R,4S,5S)-3,4-dibenzyloxy-N-tert-butyloxycarbonyl-2,5-bis(tert-butyldiphenylsilyloxymethyl)pyrrolidine

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